11,12-bis(mercaptomethyl)-9,10-dihydro-9,10-ethenoanthracene | 131760-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 11,12-bis(mercaptomethyl)-9,10-dihydro-9,10-ethenoanthracene
• 英文别名: [16-(Sulfanylmethyl)-15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaenyl]methanethiol
• CAS: 131760-75-3
• 化学式: C₁₈H₁₆S₂
• 分子量: 296.457
• InChiKey: BBOCSWXFEBNMNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11,12-bis(mercaptomethyl)-9,10-dihydro-9,10-ethenoanthracene 、 11,12-bis(bromomethyl)-9,10-dihydro-9,10-ethenoanthracene 在 氢氧化钾 作用下， 以 乙醇 、 水 、 苯 为溶剂， 以44%的产率得到5,18:9,14-di-o-benzeno-5,6,8,9,14,15,17,18-octahydrodinaphtho<2',3'-c:2",3"-h><1,6>dithiecin
  参考文献：
  名称：

  Reduction of DMAD-anthracene adducts. Synthesis and conformations of substituted cyclodecadienes

  摘要：

  A general method for reducing DMAD-anthracene adducts to the corresponding enediols is described. Thus, the ester groups of 1 were reduced without C = C reduction using the DIBAH-nBuLi ''ate'' complex to give previously unknown 2 in high yield. Analogous enediols 5-7 were similarly prepared. Base treatment of dibromide 3 and dithiol 9, both prepared from 2 by standard methods, gave conformationally rigid dithiacyclodecadiene 10. With o-, m-, and p-xylylenedithiols, dibromide 3 gave respectively the conformationally labile cyclophanes 12 and 13 and the rigid cyclophane 14. Tetrabromide 16 and dithiol 9 gave cuppedophane 17, but tetrabromide 18 and 9 formed bis-m-cyclophane 19 instead.

  DOI：

  10.1021/jo00003a019
• 作为产物：
  描述：

  11,12-bis(hydroxymethyl)-9,10-etheno-9,10-dihydroanthracene 在 2,4,6-三甲基吡啶 、 氢氧化钾 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 11,12-bis(mercaptomethyl)-9,10-dihydro-9,10-ethenoanthracene
  参考文献：
  名称：

  Reduction of DMAD-anthracene adducts. Synthesis and conformations of substituted cyclodecadienes

  摘要：

  A general method for reducing DMAD-anthracene adducts to the corresponding enediols is described. Thus, the ester groups of 1 were reduced without C = C reduction using the DIBAH-nBuLi ''ate'' complex to give previously unknown 2 in high yield. Analogous enediols 5-7 were similarly prepared. Base treatment of dibromide 3 and dithiol 9, both prepared from 2 by standard methods, gave conformationally rigid dithiacyclodecadiene 10. With o-, m-, and p-xylylenedithiols, dibromide 3 gave respectively the conformationally labile cyclophanes 12 and 13 and the rigid cyclophane 14. Tetrabromide 16 and dithiol 9 gave cuppedophane 17, but tetrabromide 18 and 9 formed bis-m-cyclophane 19 instead.

  DOI：

  10.1021/jo00003a019

文献信息

• ANANTANARAYAN, ASHOK;HART, HAROLD, J. ORG. CHEM., 56,(1991) N, C. 991-996
  作者：ANANTANARAYAN, ASHOK、HART, HAROLD

  DOI：——

  日期：——