(1S,5R,6S)-6-Formyl-bicyclo[3.1.0]hex-2-ene-1,2-dicarboxylic acid 1-ethyl ester | 122423-06-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,5R,6S)-6-Formyl-bicyclo[3.1.0]hex-2-ene-1,2-dicarboxylic acid 1-ethyl ester
• 英文别名: (1S,5R,6S)-1-ethoxycarbonyl-6-formylbicyclo[3.1.0]hex-2-ene-2-carboxylic acid
• CAS: 122423-06-7
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: NZQUFJZNNWYULI-CDOJRTKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1S,2S,4R,5R)-3-Oxa-tricyclo[3.2.1.0^2,4]oct-6-ene-6,7-dicarboxylic acid monoethyl ester 以 phosphate buffer 、 丙酮 为溶剂， 反应 4.0h， 生成 (1S,5R,6S)-6-Formyl-bicyclo[3.1.0]hex-2-ene-1,2-dicarboxylic acid 1-ethyl ester
  参考文献：
  名称：

  Asymmetric synthesis of 6-formyl-1-alkoxycarbonylbicyclo[3.1.0]hex-2-ene-2-carboxylic acids by a novel buffer-mediated rearrangement

  摘要：

  Asymmetric synthesis of 6-formyl-1-alkoxycarbonylbicyclo[3.1.0]hex-2-ene-2-carboxylic acids has been achieved and the absolute configurations of the products of a novel buffer-mediated rearrangement have been established. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00430-x

文献信息

• Revisit to meinwald rearrangement of electron-deficient systems
  作者：Satomi Niwayama、Susumu Kobayashi、Masaji Ohno

  DOI：10.1016/s0040-4039(00)82334-5

  日期：1988.1

  The monoester 6, generated in situ by the enzymatic hydrolysis of the symmetric diester 5a with pig liver esterase, undergoes extremely facile Meinwald-type rearrangement to afford the bicyclo[3.1.0]hex-2-ene derivative 8a in quantitative yield.

  通过用猪肝酯酶对对称二酯5a进行酶促水解而原位生成的单酯6，经过极为简便的Meinwald型重排，以定量收率得到双环[3.1.0] hex-2-ene衍生物8a。
• Exploration of Thermophilic Esterases/Lipases for Asymmetric Desymmetrization of Norbornane Derivatives
  作者：Yasuhiro Kashima、Jianxiu Liu、Shigeharu Takenami、Satomi Niwayama

  DOI：10.1246/bcsj.76.831

  日期：2003.4

  Asymmetric monohydrolysis of a series of norbornane derivatives by a thermophilic esterase/lipase library was examined. Three esterases/lipases showed high enantioselectivities toward dialkyl bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylates with high chemical yields.

  通过嗜热酯酶/脂肪酶文库检查了一系列降冰片烷衍生物的不对称单水解。三种酯酶/脂肪酶对二烷基双环 [2.2.1] 庚-2,5-二烯-2,3-二羧酸酯显示出高对映选择性，并具有高化学产率。
• Asymmetric synthesis of 6-formyl-1-alkoxycarbonylbicyclo[3.1.0]hex-2-ene-2-carboxylic acids by a novel buffer-mediated rearrangement
  作者：Satomi Niwayama、Jianxiu Liu

  DOI：10.1016/s0957-4166(01)00430-x

  日期：2001.10

  Asymmetric synthesis of 6-formyl-1-alkoxycarbonylbicyclo[3.1.0]hex-2-ene-2-carboxylic acids has been achieved and the absolute configurations of the products of a novel buffer-mediated rearrangement have been established. (C) 2001 Elsevier Science Ltd. All rights reserved.