(1S,2R,4S,5R)-(+)-4-hydroxybicyclo<3.1.0>hex-2-yl acetate | 137820-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,4S,5R)-(+)-4-hydroxybicyclo<3.1.0>hex-2-yl acetate
• 英文别名: (1S,2R,4S,5R)-4-hydroxybicyclo[3.1.0]hexan-2-yl acetate；[(1S,2R,4S,5R)-4-hydroxy-2-bicyclo[3.1.0]hexanyl] acetate
• CAS: 137820-15-6
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: LCDAUHCMSYLFIY-VGRMVHKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,4S,5R)-(+)-4-hydroxybicyclo<3.1.0>hex-2-yl acetate 在 吡啶 、 sodium dihydrogenphosphate 、 sodium azide 、 Electrophorus electricus acetylcholinesterase 作用下， 反应 24.0h， 生成 (1R,2S,4R,5S)-(-)-4-hydroxybicyclo<3.1.0>hex-2-yl acetate
  参考文献：
  名称：

  Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase

  摘要：

  Eight 1,3-meso-diesters derived from a common cyclopentyl backbone were exposed to the hydrolase enzyme acetylcholinesterase from Electrophorus electricus. All eight compounds were hydrolyzed by the enzyme. The overall enantioselectivities were quite high, and the resulting e.e.s were generally >90%. The absolute configurations of the product monoesters were determined through stereochemical correlation. These data revealed that the preferred site for enzymatic hydrolysis in seven of the substrates was the pro-S ester function, with pro-R cleavage detected in the eighth. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00236-0
• 作为产物：
  描述：

  在 水 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 44.0h， 生成 (1S,2R,4S,5R)-(+)-4-hydroxybicyclo<3.1.0>hex-2-yl acetate
  参考文献：
  名称：

  Lipase-catalyzed transesterification of meso-cyclopentane diols

  摘要：

  The lipase-catalyzed transesterification of the meso-cyclopentane diols 1a - 6a with vinyl acetate in tetrahydrofuran/triethylamine in the presence of lipases of different origin has been investigated. Depending on the structure of the substrate and the origin of the lipase chiral cyclopentane derivatives with high enantiomeric excess could be obtained in good to excellent chemical yields.

  DOI：

  10.1016/s0040-4020(01)88281-8

文献信息

• [EN] POLYCYCLIC-CARBAMOYLPYRIDONE COMPOUNDS AND THEIR USE FOR THE TREATMENT OF HIV INFECTIONS<br/>[FR] COMPOSÉS DE CARBAMOYLPYRIDONE POLYCYCLIQUE ET LEUR UTILISATION POUR LE TRAITEMENT DES INFECTIONS À VIH
  申请人：GILEAD SCIENCES INC

  公开号：WO2015006731A1

  公开（公告）日：2015-01-15

  Compounds for use in the treatment of human immunodeficiency virus (HIV) infection are disclosed. The compounds have the following Formula (I): including stereoisomers and pharmaceutically acceptable salts thereof, wherein R1, X, Y1, Y2, or L are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

  用于治疗人类免疫缺陷病毒（HIV）感染的化合物被披露。这些化合物具有以下通式（I）：包括立体异构体及其药学上可接受的盐，其中R1、X、Y1、Y2或L如本文所定义。还披露了与这些化合物的制备和使用相关的方法，以及包含这些化合物的药物组合物。
• Synthesis of Conformationally Locked <scp>l</scp>-Deoxythreosyl Phosphonate Nucleosides Built on a Bicyclo[3.1.0]hexane Template
  作者：Hisao Saneyoshi、Jeffrey R. Deschamps、Victor E. Marquez

  DOI：10.1021/jo101475p

  日期：2010.11.19

  l-deoxythreosyl phosphonate nucleosides (2 and 3) were synthesized to investigate the preference of HIV reverse transcriptase for a conformation displaying either a fully diaxial or fully diequatorial disposition of substituents. Synthesis of the enantiomeric 4-(6-amino-9H-purin-9-yl)bicyclo[3.1.0]hexan-2-ol carbocyclic nucleoside precursors (diaxially disposed) proceeded straightforwardly from commercially available

  合成了两个构象锁定形式的l-脱氧苏糖基膦酸酯核苷（2和3），以研究 HIV 逆转录酶对显示取代基完全双轴或完全双赤道配置的构象的偏好。对映体 4-(6-amino-9 H -purin-9-yl)bicyclo[3.1.0]hexan-2-ol 碳环核苷前体（双轴布置）的合成直接从市售 (1 R ,4 S ) 进行-4-羟基-2-环戊-2-烯基-1-基乙酸酯采用羟基导向的西蒙斯-史密斯环丙烷化反应，最终以嘌呤碱的光信偶合结束。对于更复杂的 1-(6-amino-9 H-purin-9-yl)bicyclo[3.1.0]hexan-3-ol 碳环核苷前体（diquatorially 放置），必须的线性方法需要合成关键的 1-aminobicyclo[3.1.0.]hexan-3-yl benzoate通过 Kulinkovich 反应的酰胺变体组装的前体，包括取代的 δ-乙烯基酰胺的分子内环
• POLYCYCLIC-CARBAMOYLPYRIDONE COMPOUNDS AND THEIR USE FOR THE TREATMENT OF HIV INFECTIONS
  申请人：Gilead Sciences, Inc.

  公开号：EP3019503B1

  公开（公告）日：2017-09-06
• POLYCYCLIC-CARBAMOYLPYRIDONE COMPOUNDS AND THEIR PHARMACEUTICAL USE
  申请人：Gilead Sciences, Inc.

  公开号：US20170128443A1

  公开（公告）日：2017-05-11

  Compounds for use in the treatment of human immunodeficiency virus (HIV) infection are disclosed. The compounds have the following Formula (I): including stereoisomers and pharmaceutically acceptable salts thereof, wherein R 1 , X, Y 1 , Y 2 , or L are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.
• US9421214B2
  申请人：——

  公开号：US9421214B2

  公开（公告）日：2016-08-23