1-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)naphthalene | 1388152-68-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)naphthalene
• 英文别名: 1-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl)naphthalene；1-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]naphthalene
• CAS: 1388152-68-8
• 化学式: C₂₆H₃₄
• 分子量: 346.556
• InChiKey: HIFODCPTBKOMLL-JWIKZEKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)naphthalene 在 三氟甲磺酸 、 nitrosonium trifluoromethanesulfonate 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 以78 %的产率得到(4aR,6aR,14aR,14bR,Z)-4,4,6a,14b-tetramethyl-1,4,4a,5,6,6a,13,14,14a,14b-decahydropicen-3(2H)-oneoxime
  参考文献：
  名称：

  三氟甲磺酸亚硝基酯的两个前所未有的反应：NO+ 诱导的阳离子级联环化和 C═C 氧化裂解

  摘要：

  根据结构和反应条件，亚硝酰三氟甲磺酸酯在 CH 2 Cl 2溶液中通过三种不同途径与烯烃反应：(1) 阳离子环化，(2) C=C 裂解，和 (3) 烯丙基亚硝化。描述了可能的反应途径。

  DOI：

  10.1021/acs.orglett.3c00353
• 作为产物：
  描述：

  反,反-西基乙酸 、 magnesium,2-methanidylnaphthalene,bromide 在 dilithium tetrachlorocuprate 作用下， 以 四氢呋喃 为溶剂， 反应 2.33h， 以85%的产率得到1-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)naphthalene
  参考文献：
  名称：

  Highly Enantioselective Proton-Initiated Polycyclization of Polyenes

  摘要：

  This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantio-selective proton-initiated polycyclization promoted by the 11 complex of o,o'-dichloro-BINOL and SbCl5. Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.

  DOI：

  10.1021/ja305851h

文献信息

• Highly Enantioselective Proton-Initiated Polycyclization of Polyenes
  作者：Karavadhi Surendra、E. J. Corey

  DOI：10.1021/ja305851h

  日期：2012.7.25

  This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantio-selective proton-initiated polycyclization promoted by the 11 complex of o,o'-dichloro-BINOL and SbCl5. Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.
• Two Unprecedented Reactions of Nitrosyl Triflate: NO⁺-Induced Cationic Cascade Cyclization and C═C Oxidative Cleavage
  作者：G. Sudhakar Reddy、E. J. Corey

  DOI：10.1021/acs.orglett.3c00353

  日期：2023.3.24

  Nitrosyl triflate is shown to react with olefins in a CH2Cl2 solution by three different pathways depending on structure and reaction conditions: (1) cationic cyclization, (2) C═C cleavage, and (3) allylic nitrosation. Possible reaction pathways are described.

  根据结构和反应条件，亚硝酰三氟甲磺酸酯在 CH 2 Cl 2溶液中通过三种不同途径与烯烃反应：(1) 阳离子环化，(2) C=C 裂解，和 (3) 烯丙基亚硝化。描述了可能的反应途径。