[(2R)-2-methylbut-3-enyl]sulfanylbenzene

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: [(2R)-2-methylbut-3-enyl]sulfanylbenzene
• 化学式: C₁₁H₁₄S
• 分子量: 178.298
• InChiKey: YFENGPHBEZTEJE-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [(2R)-2-methylbut-3-enyl]sulfanylbenzene 在 aluminum amalgam 、 正丁基锂 、 水 、 四丁基碘化铵 、 sodium hydride 、 间氯过氧苯甲酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 23.42h， 生成 (3S,5S,6S,8R)-6,8-Bis-benzyloxy-9,9-bis-ethylsulfanyl-3,5-dimethyl-non-1-en-5-ol
  参考文献：
  名称：

  Total Synthesis of Brevetoxin A: Part 1: First Generation Strategy and Construction of BCD Ring System

  摘要：

  Discussed herein is our first generation strategy for the total synthesis of brevetoxin A. This approach relies upon dissection of the molecule at the nine-membered ring site (ring E), A Wittig coupling of requisite polycyclic fragments 3 and 4 followed by hydroxy dithioketal cyclization was expected to furnish the polycyclic framework of brevetoxin A (1). Intermediate 8 was anticipated to be a valid synthetic precursor to phosphonium salt 3, and its synthesis was accomplished by a bis(lactonization)/thionolactone formation/functionalization sequence. In order to test our synthetic strategy, the synthesis of an advanced model system (36) was attempted. Aldehyde 38 and phosphonium salt 37 were successfully synthesized and coupled through a:Wittig reaction. Unfortunately, the planned hydroxy dithioketal cyclization to form the crucial nonacene (ring E) did not proceed as anticipated and this synthetic approach was discontinued.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<599::aid-chem599>3.0.co;2-n
• 作为产物：
  描述：

  (R)-2-methyl-3-(phenylsulfanyl)propanoic acid methyl ester 在 sodium hexamethyldisilazane 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(2R)-2-methylbut-3-enyl]sulfanylbenzene
  参考文献：
  名称：

  Total Synthesis of Brevetoxin A: Part 1: First Generation Strategy and Construction of BCD Ring System

  摘要：

  Discussed herein is our first generation strategy for the total synthesis of brevetoxin A. This approach relies upon dissection of the molecule at the nine-membered ring site (ring E), A Wittig coupling of requisite polycyclic fragments 3 and 4 followed by hydroxy dithioketal cyclization was expected to furnish the polycyclic framework of brevetoxin A (1). Intermediate 8 was anticipated to be a valid synthetic precursor to phosphonium salt 3, and its synthesis was accomplished by a bis(lactonization)/thionolactone formation/functionalization sequence. In order to test our synthetic strategy, the synthesis of an advanced model system (36) was attempted. Aldehyde 38 and phosphonium salt 37 were successfully synthesized and coupled through a:Wittig reaction. Unfortunately, the planned hydroxy dithioketal cyclization to form the crucial nonacene (ring E) did not proceed as anticipated and this synthetic approach was discontinued.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<599::aid-chem599>3.0.co;2-n

文献信息

• Total Synthesis of Brevetoxin A: Part 1: First Generation Strategy and Construction of BCD Ring System
  作者：K. C. Nicolaou、Mark E. Bunnage、Daniel G. McGarry、Shuhao Shi、Patricia K. Somers、Paul A. Wallace、Xin-Jie Chu、Konstantinos A. Agrios、Janet L. Gunzner、Zhen Yang

  DOI：10.1002/(sici)1521-3765(19990201)5:2<599::aid-chem599>3.0.co;2-n

  日期：1999.2.1

  Discussed herein is our first generation strategy for the total synthesis of brevetoxin A. This approach relies upon dissection of the molecule at the nine-membered ring site (ring E), A Wittig coupling of requisite polycyclic fragments 3 and 4 followed by hydroxy dithioketal cyclization was expected to furnish the polycyclic framework of brevetoxin A (1). Intermediate 8 was anticipated to be a valid synthetic precursor to phosphonium salt 3, and its synthesis was accomplished by a bis(lactonization)/thionolactone formation/functionalization sequence. In order to test our synthetic strategy, the synthesis of an advanced model system (36) was attempted. Aldehyde 38 and phosphonium salt 37 were successfully synthesized and coupled through a:Wittig reaction. Unfortunately, the planned hydroxy dithioketal cyclization to form the crucial nonacene (ring E) did not proceed as anticipated and this synthetic approach was discontinued.