(Z)-N-(3-methoxybenzyl)-5-tridecylidene-2-pyrrolidinone | 208844-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-N-(3-methoxybenzyl)-5-tridecylidene-2-pyrrolidinone
• 英文别名: (5Z)-1-[(3-methoxyphenyl)methyl]-5-tridecylidenepyrrolidin-2-one
• CAS: 208844-46-6
• 化学式: C₂₅H₃₉NO₂
• 分子量: 385.59
• InChiKey: BXYNADUKHUWAIO-KQWNVCNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-N-(3-methoxybenzyl)-5-tridecylidene-2-pyrrolidinone 在 DMd 、 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 丙酮 、 二氯甲烷 为溶剂， 以77%的产率得到threo-N-(3-methoxybenzyl)-5-(1-hydroxytridecyl)-2-pyrrolidinone
  参考文献：
  名称：

  Stereoselective Synthesis of 5-(1-Hydroxyalkyl)-2-pyrrolidinones Utilizing Oxidation of 5-Alkylidene-2-pyrrolidinones to Acyliminium Ion Precursors

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(00)00841-3
• 作为产物：
  描述：

  2-(4-戊炔氧基)四氢-2H-吡喃 在 六甲基磷酰三胺 、 正丁基锂 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 、 三乙胺 、 焦碳酸二乙酯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 17.0h， 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

文献信息

• 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.
• Intramolecular Cyclization of β-Alkynylpropanamides to γ-Alkylidene-γ-butyrolactams
  作者：Yuji Koseki、Shuichi Kusano、Tatsuo Nagasaka

  DOI：10.1016/s0040-4039(98)00520-6

  日期：1998.5

  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.