1,2,3,4-tetrahydronaphthalen-2-yl-2-d methanesulfonate | 443667-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydronaphthalen-2-yl-2-d methanesulfonate
• CAS: 443667-72-9
• 化学式: C₁₁H₁₄O₃S
• 分子量: 227.288
• InChiKey: GCHSTPNWXULIPY-WORMITQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydronaphthalen-2-yl-2-d methanesulfonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以56%的产率得到3-氘代-1,2-二氢萘
  参考文献：
  名称：

  Competing Regiochemical Pathways in the Heck Arylation of 1,2-Dihydronaphthalene

  摘要：

  The Heck reaction of aryl iodides with 1,2-dihydronaphthalene has been examined. Two separate reaction pathways are observed under all the conditions tried. Arylation adjacent to the aromatic ring leads to a subsequent double bond shift such that the product is a 1-aryl-1,2-dihydronaphthalene. The alternative regiochemistry leads to production of the corresponding 3-aryl-1,2-dihydronaphthalene, and labelling studies with specifically deuterated alkenes demonstrate that this is most likely to be the result of a trans Pd-H elimination pathway. The ratio always varies between 75:25 in favour of the 3-aryl product (Jeffery conditions) to 70:30 in favour of the 1-aryl product.

  DOI：

  10.1002/1615-4169(200201)344:1<104::aid-adsc104>3.0.co;2-v
• 作为产物：
  描述：

  甲基磺酰氯 、 2-deuterio-1,3,4-trihydro-2-naphthol 在 乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以83%的产率得到1,2,3,4-tetrahydronaphthalen-2-yl-2-d methanesulfonate
  参考文献：
  名称：

  Competing Regiochemical Pathways in the Heck Arylation of 1,2-Dihydronaphthalene

  摘要：

  The Heck reaction of aryl iodides with 1,2-dihydronaphthalene has been examined. Two separate reaction pathways are observed under all the conditions tried. Arylation adjacent to the aromatic ring leads to a subsequent double bond shift such that the product is a 1-aryl-1,2-dihydronaphthalene. The alternative regiochemistry leads to production of the corresponding 3-aryl-1,2-dihydronaphthalene, and labelling studies with specifically deuterated alkenes demonstrate that this is most likely to be the result of a trans Pd-H elimination pathway. The ratio always varies between 75:25 in favour of the 3-aryl product (Jeffery conditions) to 70:30 in favour of the 1-aryl product.

  DOI：

  10.1002/1615-4169(200201)344:1<104::aid-adsc104>3.0.co;2-v