(1R,2R)-(-)-2-aminoindan-1-ol | 13575-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1R,2R)-(-)-2-aminoindan-1-ol
• 英文别名: (1R,2R)-trans-2-amino-1-indanol；trans-2-Amino-2,3-dihydro-1H-inden-1-ol；(1R,2R)-2-amino-2,3-dihydro-1H-inden-1-ol
• CAS: 13575-72-9
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: HRWCWYGWEVVDLT-RKDXNWHRSA-N

物化性质

• 熔点：
  105-106 °C
• 沸点：
  296.9±40.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  (1R,2R)-(-)-2-aminoindan-1-ol 在 sodium tetrahydroborate 作用下， 以 甲醇 、 苯 为溶剂， 反应 12.0h， 生成 (+)-(6aR,11bR)-6,6a,7,11b-tetrahydro-5H-indeno<2,1-c>isoquinoline
  参考文献：
  名称：

  6,6a，7,11b-四氢-5 H-茚并[2,1-c]-异喹啉衍生物的合成及Cd光谱

  摘要：

  我们合成了具有两个半刚性空间排列的β-苯乙胺部分药效基团的标题化合物。它们非常适合研究两个芳香发色团之间电子交换作用的极限。

  DOI：

  10.1039/p19840001655
• 作为产物：
  描述：

  (1S,2S)-trans-2-amino-1-indanol 生成 (1R,2R)-(-)-2-aminoindan-1-ol
  参考文献：
  名称：

  Desimoni, Giovanni; Faita, Giuseppe; Mellerio, Giorgio, Gazzetta Chimica Italiana, 1992, vol. 122, # 5-7, p. 269 - 273

  摘要：

  DOI：

文献信息

• Enzymatic Hydroxylation by Dopamine β‐Hydroxylase
  作者：Anton A. Mitrochkine、Frank Eydoux、Gérard Gil、Marius Réglier

  DOI：10.1002/(sici)1099-0690(199806)1998:6<1171::aid-ejoc1171>3.0.co;2-#

  日期：1998.6

  three-dimensional aspects of the chemistry of dopamine β-hydroxylase (DBH) was studied through a conformationally-restricted substrate analog approach. We found that the DBH-catalyzed hydroxylation of 2-aminoindane (1) exclusively produced the trans-(1S,2S)-2-amino-1-indanol (4S) (93% ee) in contrast to the stereochemical course of the pro-R hydroxylation of the DBH/phenethylamine reaction. Studies with

  通过构象受限的底物类似物方法研究了多巴胺β-羟化酶（DBH）化学的三维方面。我们发现，DBH催化的2-氨基茚满（1）的羟化反应只产生反式-（1 S，2 S）-2-氨基-1-茚满醇（4S）（93％ee），而立体化学过程则相反。的亲- - [R的DBH /苯乙胺反应的羟基化。立体定向氘标记的2-氨基茚满2和3的研究表明（1 S）-氨基茚满醇4S的产生是立体定向pro - S夺氢，然后结合氧并保持整体构型的结果。基于这些发现，我们提出了苯乙胺底物与酶相互作用的模型。
• Cinnamide compound
  申请人：Kimura Teiji

  公开号：US20060004013A1

  公开（公告）日：2006-01-05

  The present invention relates to a compound represented by Formula (I): (wherein Ar 1 represents an imidazolyl group which may be substituted with 1 to 3 substituents; Ar 2 represents a pyridinyl group, a pyrimidinyl group, or a phenyl group which may be substituted with 1 to 3 substituents; X 1 represents (1) —C≡C— or (2) a double bond etc. which may be substituted; R 1 and R 2 represent, for example, a C1-6 alkyl group or C3-8 cycloalkyl group which may be substituted) or a pharmacologically acceptable salt thereof and to the use thereof as pharmaceutical agents. The object of the present invention is to find a therapeutic or preventive agent for diseases caused by Aβ. According to the present invention, a therapeutic or preventive agents for diseases caused by Aβ can be provided.

  本发明涉及一种由式（I）表示的化合物：（其中Ar1代表可以被1到3个取代基取代的咪唑基团；Ar2代表可以被1到3个取代基取代的吡啶基团、嘧啶基团或苯基；X1代表（1）-C≡C-或（2）可以被取代的双键等；R1和R2代表，例如，可以被取代的C1-6烷基或C3-8环烷基等）或其药理学上可接受的盐，并且用作药物剂。本发明的目的是寻找一种治疗或预防由Aβ引起的疾病的药剂。根据本发明，可以提供治疗或预防由Aβ引起的疾病的药剂。
• Process for preparing acetonides
  申请人：——

  公开号：US20020132837A1

  公开（公告）日：2002-09-19

  Acetonides are obtained in a one-step reaction of a carboxylic acid halide, a 1,2-aminoalcohol, and 2-alkoxypropene or 2,2-dialkoxypropane in an ether solvent and in the presence of an inorganic base. Acetonides are also obtained in a two-step reaction scheme in which an acid halide and 1,2-aminoalcohol are reacted in an ether solvent in the presence of LiOH to form a hydroxyamide, which is then reacted with 2-alkoxypropene or 2,2-dialkoxypropane in the presence of acid to form the acetonide. The acetonides resulting from the one-step and two-step protocols can be further reacted with an allylating agent such as an allyl halide in the presence of a strong base to provide the corresponding allyl acetonide. The acetonides and allyl acetonides can serve as intermediates in the production of certain HIV protease inhibitors which are useful for treating HIV infection and AIDS.

  Acetonides是通过在醚溶剂中，在无机碱的存在下，将羧酸卤、1,2-氨基醇和2-烷氧基丙烯或2,2-二烷氧基丙烷进行一步反应而获得的。Acetonides也可以通过两步反应方案获得，其中酸卤和1,2-氨基醇在醚溶剂中在LiOH的存在下反应以形成羟基酰胺，然后在酸的存在下与2-烷氧基丙烯或2,2-二烷氧基丙烷反应以形成缩醛。通过一步和两步方案得到的缩醛可以进一步与烯丙基卤等烯丙基化试剂在强碱的存在下反应，从而得到相应的烯丙基缩醛。这些缩醛和烯丙基缩醛可以作为某些用于治疗HIV感染和艾滋病的HIV蛋白酶抑制剂的生产中间体。
• Selective A1-adenosine receptor antagonists identified using yeast Saccharomyces cerevisiae functional assays
  作者：Robert M. Campbell、Craig Cartwright、Wei Chen、Yong Chen、Emir Duzic、Jian-Min Fu、Michelle Loveland、Ron Manning、Bryan McKibben、Christopher M. Pleiman、Lauren Silverman、Joshua Trueheart、David R. Webb、Vicki Wilkinson、David J. Witter、Xiaobing Xie、Arlindo L. Castelhano

  DOI：10.1016/s0960-894x(99)00398-4

  日期：1999.8

  Evaluation of a biased "library" of pyrrolo[2,3-d]pyrimidines using yeast-based functional assays expressing human A1- and A2a-adenosine receptors, led to the A1 selective antagonist 4b. A direct correlation between yeast functional activity and binding data was established. Practical compounds with polar residues at C-4 of the pyrrolopyrimidine system required H-bond donor functionality for high potency

  使用表达人A1-和A2a-腺苷受体的基于酵母的功能测定法评估吡咯并[2,3-d]嘧啶的偏倚“文库”，导致A1选择性拮抗剂4b。建立了酵母功能活性和结合数据之间的直接关联。在吡咯并嘧啶系统的C-4处带有极性残基的实用化合物需要H键供体官能团才能具有较高的效价。
• Stereoselective synthesis of 1,2-amino alcohols by asymmetric borane reduction of α-oxoketoxime ethers
  作者：Moriyasu Masui、Takayuki Shioiri

  DOI：10.1016/s0040-4039(98)01019-3

  日期：1998.7

  Asymmetric reduction of α-oxoketoxime ethers with the reagents prepared in situ from trimethyl borate and chiral amino alcohols derived from either L-proline or α-pinene was investigated. Both cyclic and acyclic α-oxoketoxime ethers were reduced to afford the corresponding chiral 1,2-amino alcohols with high enantioselectivities.

  研究了用由硼酸三甲酯和衍生自L-脯氨酸或α-chi烯的手性氨基醇原位制备的试剂对α-氧肟肟醚的不对称还原。环状和无环α-氧代肟醚都被还原，得到相应的具有高对映选择性的手性1,2-氨基醇。