3-(Methoxycarbonyl)-2-(2-(phenylthio)ethyl)-4,5-dihydrofuran | 131905-83-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(Methoxycarbonyl)-2-(2-(phenylthio)ethyl)-4,5-dihydrofuran
• 英文别名: methyl 5-(2-phenylsulfanylethyl)-2,3-dihydrofuran-4-carboxylate
• CAS: 131905-83-4
• 化学式: C₁₄H₁₆O₃S
• 分子量: 264.345
• InChiKey: SIZQUXMGQAKYKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(Methoxycarbonyl)-2-(2-(phenylthio)ethyl)-4,5-dihydrofuran 在 Crabtree catalyst sodium periodate 、 4,4'-硫联二(6-叔丁基-2-甲基苯酚) 、 氢气 、 calcium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 环己烷 、 水 、 乙腈 为溶剂， 反应 11.33h， 生成 rac-methyl (3aR,13bR,13cR)-1,2,4,5,7,8,13,13b-octahydrofuro[3,2-a]indolo[3,2-h]quinolizine-13c(3aH)-carboxylate
  参考文献：
  名称：

  Hexacyclic indole alkaloids. A highly convergent total synthesis of cuanzine

  摘要：

  A novel route to the hexacyclic indole alkaloid cuanzine 1 has been developed. Key synthetic steps include the cyclocondensation of the imine 8 with the dihydrofuran 10 followed by homogeneous-catalyzed hydrogenation, wherein the COOMe group at C(20) serves as a diastereocontrol element in establishing the C(15) stereogenicity. In order to define local energy minima, the conformational space of some intermediates has been explored by empirical force field calculations (MM2).

  DOI：

  10.1021/jo00007a024
• 作为产物：
  描述：

  2-(2-Benzenesulfinyl-ethyl)-4,5-dihydro-furan-3-carboxylic acid methyl ester 在 camphor-10-sulfonic acid 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以89%的产率得到3-(Methoxycarbonyl)-2-(2-(phenylthio)ethyl)-4,5-dihydrofuran
  参考文献：
  名称：

  Hexacyclic indole alkaloids. A highly convergent total synthesis of cuanzine

  摘要：

  A novel route to the hexacyclic indole alkaloid cuanzine 1 has been developed. Key synthetic steps include the cyclocondensation of the imine 8 with the dihydrofuran 10 followed by homogeneous-catalyzed hydrogenation, wherein the COOMe group at C(20) serves as a diastereocontrol element in establishing the C(15) stereogenicity. In order to define local energy minima, the conformational space of some intermediates has been explored by empirical force field calculations (MM2).

  DOI：

  10.1021/jo00007a024

文献信息

• PALMISANO, GIOVANNI;DANIELI, BRUNO;LESMA, GIORDANO;PASSARELLA, DANIELE;TO+, J. ORG. CHEM., 56,(1991) N, C. 2380-2386
  作者：PALMISANO, GIOVANNI、DANIELI, BRUNO、LESMA, GIORDANO、PASSARELLA, DANIELE、TO+

  DOI：——

  日期：——
• Hexacyclic indole alkaloids. A highly convergent total synthesis of cuanzine
  作者：Giovanni Palmisano、Bruno Danieli、Giordano Lesma、Daniele Passarella、Lucio Toma

  DOI：10.1021/jo00007a024

  日期：1991.3

  A novel route to the hexacyclic indole alkaloid cuanzine 1 has been developed. Key synthetic steps include the cyclocondensation of the imine 8 with the dihydrofuran 10 followed by homogeneous-catalyzed hydrogenation, wherein the COOMe group at C(20) serves as a diastereocontrol element in establishing the C(15) stereogenicity. In order to define local energy minima, the conformational space of some intermediates has been explored by empirical force field calculations (MM2).