(1S,5R)-3-azabicyclo<3.1.0>hexan-2-one | 154001-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1S,5R)-3-azabicyclo<3.1.0>hexan-2-one
• 英文别名: (1S,5R)-3-azabicyclo[3.1.0]hexan-2-one
• CAS: 154001-70-4
• 化学式: C₅H₇NO
• 分子量: 97.1167
• InChiKey: KHLMVJUFZYQPEP-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,5R)-3-azabicyclo<3.1.0>hexan-2-one 在 盐酸 作用下， 反应 6.0h， 生成 (1R,2S)-1-aminomethyl-2-carboxycyclopropane hydrochloride
  参考文献：
  名称：

  Synthesis of optically active cis- and trans-1,2-disubstituted cyclopropane derivatives by the Simmons-Smith reaction of allyl alcohol derivatives derived from (R)-2,3-O-isopropylideneglyceraldehyde

  摘要：

  The Simmons-Smith reactions of Z- and E-allyl alcohol derivatives 6 derived from (R)-2,3-O-isopropylideneglyceraldehyde (5) were used for the synthesis of optically active cis- and trans-1,2 disubstituted cyclopropane derivatives. Reaction of 6 with diethyl zinc and diiodomethane gave cyclopropane derivatives 7 in 84% to quantitative yields with 35 to approximate to 100% des. Identical facial selectivities toward the double bonds, Ire-asi for Z-6 and 1re-2re for E-6, were observed in the cyclopropanations. The diastereoselectivity was dependent on the protecting group on the terminal allylic oxygen (R of 6, TBDPS > MOM > Bn) and on the stereochemistry of the double bond (Z > E). For TBDPS ethers Z- and E-6c, cis- and trans-7c were obtained as single diastereomers respectively. It was clearly demonstrated that the stereoselectivity of the cyclopropanation is controlled by the directing effect of the allylic oxygen (O-1) of the dioxolane ring which coordinates to the reagent. The terminal allylic oxygen (O-2) lowered the diastereoselectivity This reaction was applied to the synthesis of optically active cyclopropane analogs of gamma-aminobutyric acid (GABA) 18, 22, and ent-22.

  DOI：

  10.1021/jo00080a017
• 作为产物：
  描述：

  cis-2-benzyloxymethyl-cyclopropanecarboxaldehyde 在 palladium on activated charcoal chromium(VI) oxide 、 sodium tetrahydroborate 、 sodium azide 、 硫酸 、 水 、 氢气 、 碳酸氢钠 、 三乙胺 、 三氟乙酸 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (1S,5R)-3-azabicyclo<3.1.0>hexan-2-one
  参考文献：
  名称：

  Synthesis of optically active cis- and trans-1,2-disubstituted cyclopropane derivatives by the Simmons-Smith reaction of allyl alcohol derivatives derived from (R)-2,3-O-isopropylideneglyceraldehyde

  摘要：

  The Simmons-Smith reactions of Z- and E-allyl alcohol derivatives 6 derived from (R)-2,3-O-isopropylideneglyceraldehyde (5) were used for the synthesis of optically active cis- and trans-1,2 disubstituted cyclopropane derivatives. Reaction of 6 with diethyl zinc and diiodomethane gave cyclopropane derivatives 7 in 84% to quantitative yields with 35 to approximate to 100% des. Identical facial selectivities toward the double bonds, Ire-asi for Z-6 and 1re-2re for E-6, were observed in the cyclopropanations. The diastereoselectivity was dependent on the protecting group on the terminal allylic oxygen (R of 6, TBDPS > MOM > Bn) and on the stereochemistry of the double bond (Z > E). For TBDPS ethers Z- and E-6c, cis- and trans-7c were obtained as single diastereomers respectively. It was clearly demonstrated that the stereoselectivity of the cyclopropanation is controlled by the directing effect of the allylic oxygen (O-1) of the dioxolane ring which coordinates to the reagent. The terminal allylic oxygen (O-2) lowered the diastereoselectivity This reaction was applied to the synthesis of optically active cyclopropane analogs of gamma-aminobutyric acid (GABA) 18, 22, and ent-22.

  DOI：

  10.1021/jo00080a017

文献信息

• [EN] PLASMA KALLIKREIN INHIBITORS<br/>[FR] INHIBITEURS DE LA KALLICRÉINE PLASMATIQUE
  申请人：MERCK SHARP & DOHME

  公开号：WO2021257353A1

  公开（公告）日：2021-12-23

  The present invention provides a compound of Formula (I) and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing one or more disease states that could benefit from inhibition of plasma kallikrein, including hereditary angioedema, uveitis, posterior uveitis, wet age related macular edema, diabetic macular edema, diabetic retinopathy and retinal vein occlusion. The compounds are selective inhibitors of plasma kallikrein.

  本发明提供了一种式(I)的化合物，以及包括一种或多种所述化合物的药物组合物，并且使用所述化合物治疗或预防可能受益于抑制血浆激肽酶的一种或多种疾病状态的方法，包括遗传性血管性水肿、葡萄膜炎、后部葡萄膜炎、湿性老年性黄斑水肿、糖尿病性黄斑水肿、糖尿病视网膜病变和视网膜静脉阻塞。这些化合物是血浆激肽酶的选择性抑制剂。
• Rh(II)-catalyzed asymmetric cyclopropenation of propargyl derivatives; synthesis of cyclopropene- and cis-cyclopropane-amino acids
  作者：Paul Müller、Hassan Imogaı̈

  DOI：10.1016/s0957-4166(98)00469-8

  日期：1998.12

  The [Rh-2(2S)-mepy}(4)]-catalyzed cyclopropenation of propargylamines carrying two carboxyl or sulfonyl protecting groups with ethyl diazoacetate proceeds in high yield and with enantioselectivities in the range of 90->97% ee. Selective deprotection of the TEOC-derivative afforded ethyl 2-aminomethylcycloprop-2-ene-1-carboxylate which was converted to several analogs of gamma-aminobutyric acid (GABA) containing the cyclopropene or cyclopropane ring. (C) 1998 Elsevier Science Ltd. All rights reserved.