2,2,2-trichloroethyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate | 294198-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2,2-trichloroethyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate
• 英文别名: 2,2,2-trichloroethyl (E,4R,5S)-5-hydroxy-4-phenylmethoxyhex-2-enoate
• CAS: 294198-50-8
• 化学式: C₁₅H₁₇Cl₃O₄
• 分子量: 367.657
• InChiKey: YQXAWMBAWVAYDY-GPTOWFIXSA-N

物化性质

• 沸点：
  494.0±45.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 在 4-二甲氨基吡啶 、 三氯化铝 、 (+)-comphorsulfonic acid 、 4 A molecular sieve 、 AcOH-AcONa buffer 、 2,4,6-三氯苯甲酰氯 、 溶剂黄146 、 (+)-10-camphorsulfonic acid 、 三乙胺 、 间二甲苯 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 178.5h， 生成 macrosphelide E
  参考文献：
  名称：

  Total syntheses of macrosphelides (+)-A, (−)-A and (+)-E

  摘要：

  Total syntheses of (+)-macrosphelide A 1 (18.5% overall yield in 11 steps) and (+)-macrosphelide E 2 (23.9% overall yield in 11 steps) have been achieved via the chemoenzymatic reaction product (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 4. The enantiomer (-)-A (1) (14.2% overall yield in 11 steps) of (+)-1 was also synthesized from the chemoenzymatic reaction product (4S,SR)-4-benzyloxy-5-hydroxy-2(E)hexenoate 4. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00245-7
• 作为产物：
  描述：

  methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 101.5h， 生成 2,2,2-trichloroethyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate
  参考文献：
  名称：

  Total syntheses of macrosphelides (+)-A, (−)-A and (+)-E

  摘要：

  Total syntheses of (+)-macrosphelide A 1 (18.5% overall yield in 11 steps) and (+)-macrosphelide E 2 (23.9% overall yield in 11 steps) have been achieved via the chemoenzymatic reaction product (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 4. The enantiomer (-)-A (1) (14.2% overall yield in 11 steps) of (+)-1 was also synthesized from the chemoenzymatic reaction product (4S,SR)-4-benzyloxy-5-hydroxy-2(E)hexenoate 4. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00245-7

文献信息

• New total syntheses of (+)-macrosphelides C, F and G
  作者：Hiroshi Nakamura、Machiko Ono、Yuki Shida、Hiroyuki Akita

  DOI：10.1016/s0957-4166(02)00180-5

  日期：2002.5

  The total synthesis of (+)-macrosphelide C 1 (25% overall yield in nine steps), (+)-macrosphelide F 2 (20% overall yield in nine steps) and (+)-macrosphelide G 3 (22% overall yield in nine steps) has been achieved from the chemoenzymatic reaction product (4R,5S)-4-benyloxy-5-hydroxy-(2E)-hexenoate 7. (C) 2002 Published by Flsevier Science Ltd.
• Formal Total Synthesis of Macrosphelide (+)-A, Effect on Marcolactonization Depended upon the Lactone Formation Position
  作者：Hiroyuki Akita、Hiroshi Nakamura、Machiko Ono、Miho Makino

  DOI：10.3987/com-01-9391

  日期：——
• Total syntheses of macrosphelides (+)-A, (−)-A and (+)-E
  作者：Machiko Ono、Hiroshi Nakamura、Fumi Konno、Hiroyuki Akita

  DOI：10.1016/s0957-4166(00)00245-7

  日期：2000.7

  Total syntheses of (+)-macrosphelide A 1 (18.5% overall yield in 11 steps) and (+)-macrosphelide E 2 (23.9% overall yield in 11 steps) have been achieved via the chemoenzymatic reaction product (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 4. The enantiomer (-)-A (1) (14.2% overall yield in 11 steps) of (+)-1 was also synthesized from the chemoenzymatic reaction product (4S,SR)-4-benzyloxy-5-hydroxy-2(E)hexenoate 4. (C) 2000 Elsevier Science Ltd. All rights reserved.