(1R,4S)-3-Formyl-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid ethyl ester | 189345-94-6

• 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: (1R,4S)-3-Formyl-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid ethyl ester
• 英文别名: ethyl (1R,4S)-3-formylbicyclo[2.2.1]hepta-2,5-diene-2-carboxylate
• CAS: 189345-94-6
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: OKHWTXNMISWCTP-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4S)-3-Formyl-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid ethyl ester 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 18.0h， 生成 ethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate
  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
• 作为产物：
  描述：

  (1R,4S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid ethyl ester 在 sodium periodate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 50.0h， 生成 (1R,4S)-3-Formyl-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid 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

• First Enantioselective Catalytic Diels−Alder Reaction of Dienes and Acetylenic Aldehydes:  Experimental and Theoretical Evidence for the Predominance of <i>Exo</i>-Transition Structure
  作者：Kazuaki Ishihara、Shoichi Kondo、Hideki Kurihara、Hisashi Yamamoto、Shigenori Ohashi、Satoshi Inagaki

  DOI：10.1021/jo970171v

  日期：1997.5.1
• 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.