(2R)-(+)-桥-降冰片 | 61277-90-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (2R)-(+)-桥-降冰片
• 中文别名: (1S,2R,4R)-二环[2.2.1]庚烷-2-醇
• 英文名称: exo-norborneol
• 英文别名: (1S)-Bicyclo<2.2.1>heptan-endo-2-ol；(+)-endo-Bicyclo<2.2.1>heptan-2-ol；(R)-(+)-endo-2-norborneol；(+)-(R)-endo-norborneol；(1S,2R,4R)-2-norborneol；(+)-endo-2-norborneol；endo-Bicyclo[2.2.1]heptan-2-ol；(1S,2R,4R)-bicyclo[2.2.1]heptan-2-ol
• CAS: 61277-90-5；497-36-9
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: ZQTYQMYDIHMKQB-DSYKOEDSSA-N

物化性质

• 熔点：
  149-154 °C(lit.)
• 沸点：
  176.5±0.0℃ (760 Torr)
• 密度：
  1.097±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  74.4±10.9℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25
• 危险类别码：
  R24/25
• 海关编码：
  2906199090

反应信息

• 作为反应物：
  描述：

  (2R)-(+)-桥-降冰片 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,4R)-bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Discovery of dual Axl/VEGF-R2 inhibitors as potential anti-angiogenic and anti-metastatic drugs for cancer chemotherapy

  摘要：

  Axl tyrosine kinase has been shown to be involved in multiple pathways contributing to tumor development, angiogenesis, and metastasis. High Axl expression has been observed in many human tumors where it appears to confer aggressive tumor behavior. Here we present several series of dual Axl-VEGF-R2 kinase inhibitors based on extensive optimization of an acyl diaminotriazole. It was hypothesized that dual inhibition of these two receptor tyrosine kinases may have a synergistic affect in inhibiting tumor angiogenesis and metastasis. One of these molecules, R916562 showed comparable activity to Sunitinib in two mouse tumor xenograft models and a mouse corneal micropocket model. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.06.071
• 作为产物：
  描述：

  在 palladium on activated charcoal 水 、 氢气 作用下， 生成 (2R)-(+)-桥-降冰片
  参考文献：
  名称：

  2-Norbornanediazonium ions revisited

  摘要：

  DOI：

  10.1021/ja00342a051

文献信息

• Processes and intermediates in the synthesis of 5-(3-exo-bicyclo&lsqb;2.2.1&rsqb;hept-2-yloxy-4-methoxyphenyl)-3,4,5,6-tetrahydropyrimidine-2(1H)-one
  申请人：Pfizer INC

  公开号：US06399776B2

  公开（公告）日：2002-06-04

  This invention relates to novel processes for preparing the pharmaceutically active compound 5-(3-[(2S)-exo-bicyclo[2.2.1]hept-2-yloxy]-4-methoxyphenyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one and its corresponding 2R enantiomer and for preparing certain intermediates used in the synthesis of these compounds. It also relates to novel intermediates used in the synthesis of such pharmaceutically active compounds and to other novel compounds that are related to such intermediates.

  这项发明涉及制备药用活性化合物5-(3-[(2S)-外消旋双环[2.2.1]庚-2-氧基]-4-甲氧基苯基)-3,4,5,6-四氢嘧啶-2(1H)-酮及其对应的2R对映体的新工艺，以及制备用于合成这些化合物的某些中间体。它还涉及用于合成此类药用活性化合物的新中间体，以及与这些中间体相关的其他新化合物。
• Bioorganometallic chemistry: Co-factor regeneration, enzyme recognition of biomimetic 1,4-NADH analogs, and organic synthesis; tandem catalyzed regioselective formation of N-substituted-1,4-dihydronicotinamide derivatives with [Cp*Rh(bpy)H]+, coupled to chiral S-alcohol formation with HLADH, and engineered cytochrome P450s, for selective C-H oxidation reactions
  作者：H. Christine Lo、Jessica D. Ryan、John B. Kerr、Douglas S. Clark、Richard H. Fish

  DOI：10.1016/j.jorganchem.2017.02.013

  日期：2017.6

  tandem catalysis approaches for the chiral synthesis of S-alcohols from reduction of their prochiral ketones with Horse Liver Alcohol Dehydrogenase (HLADH), and selective C-H oxidation reactions with protein engineered Cytochrome P450s, are presented. We utilized a co-factor regeneration procedure with three biomimetic NAD+ models that do not contain the pyrophosphate, nor the adenosine group, and either/or

  提出了两种新的串联催化方法，用于通过用马肝酒精脱氢酶（HLADH）还原手性酮来手性合成S醇，以及使用蛋白质工程化的细胞色素P450进行选择性CH氧化反应。我们使用了一种辅因子再生程序，使用了三个不包含焦磷酸盐，也不包含腺苷基团和/或核糖的N-1-苄基烟酰胺三氟甲磺酸盐1，N-4-甲氧基苄基烟酰胺三氟甲磺酸盐2的仿生NAD +模型。，以及β-烟酰胺5'-核糖磷酸甲酯3，与从[Cp * Rh（bpy）（H 2 O）]原位形成的[Cp * Rh（bpy）H] +2+（CP * =η 5 -C 5我5，联吡啶= 2,2'-联吡啶）和氢化物源，甲酸钠，以区域选择性提供他们的1,4- NADH类似物，ñ -苄基-1,4-二氢烟碱酰胺4，N-4-甲氧基苄基-1,4-二氢烟碱酰胺5和1,4-二氢烟碱酰胺-5'-核糖甲基磷酸盐6。令人惊讶的是，在第二种串联催化方法中，天然的1,4-NADH依赖性酶HLADH识别了1
• BF₃·OEt₂-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles
  作者：Chuangchuang Xu、Jiaxi Xu

  DOI：10.1039/c9ob02428j

  日期：——

  Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ

  实现了串联的梅因瓦尔德重排和亲核取代的环氧乙烷腈。在微波辐射下，在三氟化硼的存在下，由3-芳基环氧乙烷-2-甲腈与胺，醇或水容易地合成丙烯酸酯衍生物，设计的合成策略包括将氰基离去基团引入芳基环氧化物中并捕获原位生成的化合物。有毒的氰化物与三氟化硼，使反应高效，安全且对环境无害。该反应通过酸促进的Meinwald重排发生，产生芳基乙酰基氰化物，然后与含氮或氧的亲核胺，醇或水进行加成-消除过程。当前方法为串联Meinwald重排提供了新的应用。
• Enzymatic resolution of norbornane-type esters
  作者：Th. Oberhauser、M. Bodenteich、K. Faber、G. Penn、H. Griengl

  DOI：10.1016/s0040-4020(01)81675-6

  日期：1987.1

  Chiral norbornane-type alcohols of high optical purity were prepared via enzymatic resolution of their racemic esters using lipases from Candida cylindracea and Pseudomonas sp. This method presents a short and efficient access to a number of chiral building blocks on a molar scale for the synthesis of optically active cyclopentane systems.

  高光学纯度的手性降冰片烷型醇是通过使用Candida cylindracea和Pseudomonas sp的脂肪酶通过消旋外消旋酯的酶解制备的。该方法提供了一种短而有效的方法，可以以摩尔级规模接近许多手性结构单元，用于合成旋光性环戊烷体系。
• Trisubstituted-N-[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl] benzamides which inhibit P2X3 and P2X2/3 containing receptors
  申请人：——

  公开号：US20020173665A1

  公开（公告）日：2002-11-21

  Compounds of formula (I) 1 are novel P2X 3 and P2X 2 /P2X 3 antagonists which are useful in treating pain, urinary incontinence and bladder overactivity.

  化合物的式(I)1是新颖的P2X3和P2X2/P2X3拮抗剂，可用于治疗疼痛、尿失禁和膀胱过度活动。