(3S,5Z)-3-(tert-butoxycarbonylamino)tetradec-5-enoic acid methyl ester | 318466-93-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S,5Z)-3-(tert-butoxycarbonylamino)tetradec-5-enoic acid methyl ester
• 英文别名: methyl (Z,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]tetradec-5-enoate
• CAS: 318466-93-2
• 化学式: C₂₀H₃₇NO₄
• 分子量: 355.518
• InChiKey: NFCDOQDTJXJDOV-NJWFCXLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5Z)-3-(tert-butoxycarbonylamino)tetradec-5-enoic acid methyl ester 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (Z)-(S)-3-Amino-tetradec-5-enoic acid methyl ester
  参考文献：
  名称：

  Efficient macrocyclization by means of 2-nitrobenzenesulfonamide and total synthesis of lipogrammistin-A

  摘要：

  Synthesis of medium- and large-sized cyclic amines using alkylation with 2-nitrobenzenesulfonamides is described. Using either conventional alkylation procedures or Mitsunobu conditions, the cyclization reaction proceeded in a highly efficient manner. The usefulness of this methodology has been fully demonstrated in the total synthesis of lipogrammistin-A (9), an 18-membered cyclic polyamine. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00626-9
• 作为产物：
  描述：

  nonyltriphenylphosphonium iodide 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 生成 (3S,5Z)-3-(tert-butoxycarbonylamino)tetradec-5-enoic acid methyl ester
  参考文献：
  名称：

  Efficient macrocyclization by means of 2-nitrobenzenesulfonamide and total synthesis of lipogrammistin-A

  摘要：

  Synthesis of medium- and large-sized cyclic amines using alkylation with 2-nitrobenzenesulfonamides is described. Using either conventional alkylation procedures or Mitsunobu conditions, the cyclization reaction proceeded in a highly efficient manner. The usefulness of this methodology has been fully demonstrated in the total synthesis of lipogrammistin-A (9), an 18-membered cyclic polyamine. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00626-9

文献信息

• Fujiwara; Kan; Fukuyama, Synlett, 2000, # 11, p. 1667 - 1669
  作者：Fujiwara、Kan、Fukuyama

  DOI：——

  日期：——
• Absolute Structure and Total Synthesis of Lipogrammistin-A, a Lipophilic Ichthyotoxin of the Soapfish
  作者：Hiroyuki Onuki、Kei Ito、Yoshimasa Kobayashi、Nobuaki Matsumori、Kazuo Tachibana、Nobuhiro Fusetani

  DOI：10.1021/jo9722461

  日期：1998.6.1

  Lipogrammistin-A (Ib) was isolated as an ichthyotoxic and hemolytic constituent of the skin mucus of the grammistid fish Aulacocephalus temmincki. Its absolute stereochemistry was established by chemical degradation and total synthesis. The stereochemistry of the 2-methylbutyryl moieties attached to N9 and N15 was determined to be S by HPLC analysis of a diastereomeric derivative. The stereochemistry of the remaining C4 position was elucidated to be S by a total synthesis of the two diastereomers (4S)- and (4R)-1.
• Efficient macrocyclization by means of 2-nitrobenzenesulfonamide and total synthesis of lipogrammistin-A
  作者：Toshiyuki Kan、Akiko Fujiwara、Hideki Kobayashi、Tohru Fukuyama

  DOI：10.1016/s0040-4020(02)00626-9

  日期：2002.8

  Synthesis of medium- and large-sized cyclic amines using alkylation with 2-nitrobenzenesulfonamides is described. Using either conventional alkylation procedures or Mitsunobu conditions, the cyclization reaction proceeded in a highly efficient manner. The usefulness of this methodology has been fully demonstrated in the total synthesis of lipogrammistin-A (9), an 18-membered cyclic polyamine. (C) 2002 Published by Elsevier Science Ltd.