heptadec-4-ynoic acid | 208844-50-2

• 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: heptadec-4-ynoic acid
• CAS: 208844-50-2
• 化学式: C₁₇H₃₀O₂
• 分子量: 266.424
• InChiKey: QEXKSLMUNYUCEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  19.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  heptadec-4-ynoic acid 在 silver trifluoromethanesulfonate 、 三乙胺 、 焦碳酸二乙酯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 (Z)-N-(3-methoxybenzyl)-5-tridecylidene-2-pyrrolidinone
  参考文献：
  名称：

  Intramolecular Cyclization of β-Alkynylpropanamides to γ-Alkylidene-γ-butyrolactams

  摘要：

  A general method for the base-catalized intramolecular cyclization of beta-alkynylpropanamides 1 to gamma-alkylidene-gamma-butyrolactames 2 (and 3) was established. Reactions of beta-alkynylamides 1c-h, possessing alkyl groups at the terminal acetylenes, in the presence of a catalytic amount of LiN(TMS)(2)/AgOTf (= 2:1) in toluene gave exclusively (Z)-alkylidenelactames 2c-h in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00520-6
• 作为产物：
  描述：

  heptadec-4-yn-1-ol 生成 heptadec-4-ynoic acid
  参考文献：
  名称：

  Intramolecular Cyclization of β-Alkynylpropanamides to γ-Alkylidene-γ-butyrolactams

  摘要：

  A general method for the base-catalized intramolecular cyclization of beta-alkynylpropanamides 1 to gamma-alkylidene-gamma-butyrolactames 2 (and 3) was established. Reactions of beta-alkynylamides 1c-h, possessing alkyl groups at the terminal acetylenes, in the presence of a catalytic amount of LiN(TMS)(2)/AgOTf (= 2:1) in toluene gave exclusively (Z)-alkylidenelactames 2c-h in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00520-6

文献信息

• Concise stereoselective total synthesis of (+)-muricatacin and (+)<i>-epi-</i>muricatacin
  作者：Hong-Bo Dong、Ming-Yan Yang、Bin Liu、Ming-An Wang

  DOI：10.1080/10286020.2014.916695

  日期：2014.8.3

  Efficient stereoselective total synthesis of (+)-muricatacin (1) and (+)-epi-muricatacin (8) was accomplished from commercially available chemical pent-4-ynoic acid via Shi's asymmetric epoxidation and Mitsunobu reaction as the key steps in 17.8% and 26.9% overall yields, respectively.

  有效的立体选择性全合成（+）-muricatacin（1）和（+）- epi- muricatacin（8）是由市售的化学戊-4-炔酸通过Shi的不对称环氧化和Mitsunobu反应完成的，这是17.8％的关键步骤和26.9％的总收益率。
• Stereoselective Synthesis of 5-(1-Hydroxyalkyl)-2-pyrrolidinones Utilizing Oxidation of 5-Alkylidene-2-pyrrolidinones to Acyliminium Ion Precursors
  作者：Yuji Koseki、Shuichi Kusano、Daisuke Ichi、Keiji Yoshida、Tatsuo Nagasaka

  DOI：10.1016/s0040-4020(00)00841-3

  日期：2000.11

  A general method was devised for the LiN(TMS)(2)/AgOTf (=2:1)-catalyzed intramolecular (5-exo-dig) cyclization of beta -alkynylamides 1 possessing alkyl, aryl or no functional groups at the terminal alkynes, to 5-alkylidene-2-pyrrolidinones 2. These 5-alkylidene-2-pyrrolidinones were oxidized to the diol-type alkoxylactams 3 by dimethyldioxirane (DMD) or mCPBA in MeOH. These alkoxylactams are useful as tertiary N-acyliminium ion precursors for the synthesis of threo-5-(1-hydroxyalkyl)-2-pyrrolidinone derivatives 5. (C) 2000 Elsevier Science Ltd. All rights reserved.