(1R)-5-甲氧基-1,2,3,4-四氢萘-1-基)胺 | 103882-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (1R)-5-甲氧基-1,2,3,4-四氢萘-1-基)胺
• 英文名称: (R)-(-)-5-methoxy-1,2,3,4-tetrahydro-1-naphthalenamine
• 英文别名: R-5-methoxy-1-tetraline amine；(1R)-5-Methoxy-1,2,3,4-tetrahydronaphthalen-1-amine
• CAS: 103882-27-5
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: WGLJGXBRZQHFBR-SNVBAGLBSA-N

物化性质

• 沸点：
  298.1±40.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R)-5-甲氧基-1,2,3,4-四氢萘-1-基)胺 在 sodium tetrahydroborate 、 三溴化硼 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Discovery of new diphenyloxazole derivatives containing a pyrrolidine ring: Orally active prostacyclin mimetics. Part 2

  摘要：

  Synthetic and biological evaluation of novel diphenyloxazole derivatives containing a pyrrolidine ring, as a prostacyclin mimetic without the PG skeleton, are described. Asymmetric reduction of a ketone using a chiral Ru complex and reductive amination by NaBH4 produces four isomers of the tetrahydronaphthalene ring and the pyrrolidine ring with high stereoselectivity. FR193262 (4), (R,R)-diphenyloxazolyl pyrrolidine derivative, displays high potency and agonist efficacy at the IP receptor and has good bioavailability in rats and dogs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.042
• 作为产物：
  描述：

  5-甲氧基-1-四氢萘胺 生成 (1R)-5-甲氧基-1,2,3,4-四氢萘-1-基)胺
  参考文献：
  名称：

  1-Aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)alkyl]piperazines and Their Analogues:  Influence of the Stereochemistry of the Tetrahydronaphthalen-1-yl Nucleus on 5-HT_1A Receptor Affinity and Selectivity versus α₁ and D₂ Receptors. 5

  摘要：

  Some 1-aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazines and their alkylamino and alkylamido analogues, previously studied as 5-HT1A ligands, were prepared in enantiomerically pure form, and their absolute configuration was det;ermined by chemical correlation or by chiroptical properties. They were evaluated for in vitro 5-HT1A, D-2, and alpha(1) receptor affinity by radioligand binding assays, to study the influence of the chiral carbon atom of the tetrahydronaphthalene nucleus on the 5-HT1A affinity and selectivity. Results indicated that, as regarding the 5-HT1A receptor affinity, there was no difference in affinity between (-)- and (+)-enantiomers as well as the racemate of each compound. The stereochemistry, instead, influenced the selectivity: all (-)-enantiomers displayed affinity values higher than those of (+)-isomers at D-2 receptors, and conversely, all (+)-enantiomers displayed affinity values higher than those of (-)-isomers at alpha(1) receptors. As a result of this trend, it is not possible to predict the isomer with a better selectivity profile. However, compounds (S)-(+)-2, (S)-(+)-4, and (R)-(+)-6 displayed high affinity for the 5-HT1A receptor (IC50 values ranging between 7.0 and 2.3 nM) and good selectivity (greater than or equal to 250-fold) versus both D-2 and alpha(1) receptors. Furthermore, compounds (S)-(+)-4 and (R)-(-)-4 were submitted to the [S-35]GTP gamma S binding assay for a preliminary evaluation of their intrinsic activity on the 5-HT1A receptor.

  DOI：

  10.1021/jm980420n

文献信息

• 一种光学纯手性胺的制备方法
  申请人：王际菊

  公开号：CN106380408A

  公开（公告）日：2017-02-08

  本发明公开了一种光学纯手性胺R‑5‑甲氧基‑1‑萘满胺的制备方法。具体方法是：原料5‑甲氧基‑1‑萘满酮经还原氨化得消旋5‑甲氧基‑1‑萘满胺，外消旋胺再酶催化的动态动力学拆分得R‑5‑甲氧基‑1‑萘满胺。本发明具备操作简单、原料易得、产品收率好、光学纯度高等特点。
• Aromatic amides and ureas and their uses as sweet and/or umami flavor modifiers, tastants and taste enhancers
  申请人：Tachdjian Catherine

  公开号：US20060045953A1

  公开（公告）日：2006-03-02

  The inventions disclosed herein relate to non-naturally occurring amide compounds that are capable, when contacted with comestible food or drinks or pharmaceutical compositions at concentrations preferably on the order of about 100 ppm or lower, of serving as savory (“umami”) or sweet taste modifiers, savory or sweet flavoring agents and savory or sweet flavor enhancers, for use in foods, beverages, and other comestible or orally administered medicinal products or compositions, optionally in the presence of or in mixtures with conventional flavoring agents such as monosodium glutamate or known natural and artificial sweeteners.

  本发明涉及非自然存在的酰胺化合物，当与可食用食品或饮料或制药组成物以浓度优选为大约100 ppm或更低的浓度接触时，能够作为可口（"鲜味"）或甜味调节剂、可口或甜味调味剂和可口或甜味增强剂，在食品、饮料和其他可食用或口服药物或组成物中使用，可选地与常规调味剂如味精或已知的天然和人造甜味剂混合使用。
• Molecules comprising linked organic moieties as flavor modifiers for comestible compositions
  申请人：Tachdjian Catherine

  公开号：US20060257543A1

  公开（公告）日：2006-11-16

  The inventions disclosed herein relate to genuses of non-naturally occurring small molecule compounds which comprise two or optionally three organic moieties of limited size “linked” by certain structurally related “linker” functional groups. Suitable linker groups include ester, amine, ether, keto, imino, thioamide, thioether, sulfonamide, sulfonate ester, sulfone, guanidine, and thiourea groups. The compounds are capable, when contacted with comestible food or drinks or pharmaceutical compositions, at concentrations preferably on the order of about 100 ppm or lower, of serving as savory (“umami”) or sweet taste modifiers, savory or sweet flavoring agents and savory or sweet flavor enhancers, for use in foods, beverages, and other comestible or orally administered medicinal products or compositions, optionally in the presence of or in mixtures with conventional flavoring agents such as monosodium glutamate or known natural or artificial sweeteners.

  本发明涉及一类非自然产生的小分子化合物属，其包括两个或可选的三个有限大小的有机基团，由某些结构相关的“连接”功能基团“连接”而成。适当的连接基团包括酯、胺、醚、酮、亚胺、硫酰胺、硫醚、磺酰胺、磺酸酯、砜、鸟氨酸和硫脲基团。当与可食用食品或饮料或药物组成物接触时，这些化合物能够在浓度优选在约100 ppm或更低的情况下，作为鲜味（"鲜味"）或甜味调味剂，鲜味或甜味调味剂和鲜味或甜味增强剂，用于食品、饮料和其他可食用或口服药物产品或组成物，可选地与常规调味剂如谷氨酸钠或已知的天然或人造甜味剂混合使用。
• N6-substituted adenosines
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0179667A2

  公开（公告）日：1986-04-30

  There is disclosed a compound of the following general formula (I): its diastereomer, or a pharmaceutically acceptable acid addition salt thereof; wherein R1 is of the formula or in which; n is an integer of from one to four; Z is hydrogen, lower alkyl or hydroxy; Y is hydrogen, lower alkyl, or OR where R is hydrogen, lower alkyl or lower alkanoyl; A is a bond or a straight or branched alkylene of from one to four carbon atoms, with the proviso that A cannot be a bond when R1 is of Formula II and n is one; X and X' are each, independently, hydrogen, lower alkyl, lower alkoxy, hydroxy, lower alkanoyl, nitro, trifluoromethyl, halogen, amino, monolower-alkyl or diloweralkylamino, or when taken X and X' together are a methylenedioxy group; R2 is a) hydrogen, b) halogen, c) NR'R" where R' and R" are independently hydrogen, lower alkyl, phenyl, or phenyl substituted by lower alkyl, lower alkoxy, halogen, or trifluoromethyl, d) SR'" where R" is hydrogen, lower alkyl, lower alkanoyl, benzoyl, or phenyl; R'2, R'3 and R'e are each, independently, hydrogen, alkanoyl having two to twelve carbon atoms, inclusive, in a straight or branched alkyl chain, benzoyl, or benzoyl substituted by lower alkyl, lower alkoxy, halogen, or R'2 and R'3 taken together are a five- membered ring having a total of up to twenty carbons; or R'e is, independently, a phosphate, hydrogen, or dihydrogen phosphate, or an alkali metal or ammonium, or dialkali or diammonium salt thereof; with the proviso that overall when R1 is II and X' X', Y, and Z are hydrogen, or lower alkyl then n cannot be two. The novel N6-substituted adenosines have desirable ratio of affinities at A1 or A2 receptors and highly desirable central nervous system and cardiovascular activities, such as analgesic, antipsychotic, sedative, or antihypertensive as well as immunoinflammatory activity.

  本发明公开了一种通式（I）如下的化合物： 其非对映异构体，或其药学上可接受的酸 加成盐； 其中 R1 为式 或 其中 n 是 1 到 4 的整数； Z 是氢、低级烷基或羟基； Y 是氢、低级烷基或 OR，其中 R 是氢、低级烷基或低级烷酰基； A 是键或 1 至 4 个碳原子的直链或支链亚烷基，但当 R1 为式 II 且 n 为 1 时，A 不能为键； X和X'各自独立地为氢、低级烷基、低级烷氧基、羟基、低级烷酰基、硝基、三氟甲基、卤素、氨基、单低级烷基或稀低烷基氨基，或当X和X'合在一起时为亚甲基二氧基； R2 是 a) 氢，b) 卤素，c) NR'R"，其中 R' 和 R "独立地是氢、低级烷基、苯基或被低级烷基、低级烷氧基、卤素或三氟甲基取代的苯基，d) SR'"，其中 R" 是氢、低级烷基、低级烷酰基、苯甲酰基或苯基； R'2、R'3 和 R'e 各自独立地是氢、在直链或支链烷基中具有 2 至 12 个碳原子的烷酰基、苯甲酰基或被低级烷基、低级烷氧基、卤素取代的苯甲酰基，或 R'2 和 R'3 合在一起是一个总碳数不超过 20 个的五元环；或 R'e 独立地是磷酸、氢或磷酸二氢、或碱金属或铵、或二碱或二铵盐；但总体上，当 R1 是 II 且 X' X'、Y 和 Z 是氢、或低级烷基时，则 n 不能为 2。 新型 N6 取代腺苷在 A1 或 A2 受体上具有理想的亲和力比率，并具有非常理想的中枢神经系统和心血管活性，如镇痛、抗精神病、镇静或抗高血压以及免疫炎症活性。
• Amino-1,3,5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof, and their use as herbicides and plant growth regulators.
  申请人：Bayer CropScience AG

  公开号：EP2305655A2

  公开（公告）日：2011-04-06

  Amino-1,3,5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof, and their use as herbicides and plant growth regulators. The invention relates to an optically active compound of formula (I) or a salt thereof: wherein the various symbols are as defined in the description, to proceses for their preparation, to compositions thereof, and to their use as herbicides or plant growth regulators. The invention also relates to novel intermediates of formula (III), (V) and (XIII) as defined in the description.

  N-取代手性双环基的氨基-1,3,5-三嗪、其制备工艺、其组合物及其作为除草剂和植物生长调节剂的用途。 本发明涉及一种具有光学活性的式 (I) 化合物或其盐： 其中各种符号如描述中所定义，涉及其制备工艺、其组合物及其作为除草剂或植物生长调节剂的用途。本发明还涉及如描述中所定义的式 (III)、(V) 和 (XIII) 的新型中间体。