1-[(1S)-3-氯-1-苯基丙氧基]-2-甲基苯 | 114446-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-[(1S)-3-氯-1-苯基丙氧基]-2-甲基苯
• 英文名称: -(+)-1-chloro-3-phenyl-3-(2-methylphenoxy)propane
• 英文别名: (S)-2-(3-Cloro-1-phenylpropoxy)-1-methylbenzene；[S]-(+)-1-Chloro-3-phenyl-3-(2-methylphenoxy)propane；1-[(1S)-3-Chloro-1-phenylpropoxy]-2-methylbenzene
• CAS: 114446-50-3
• 化学式: C₁₆H₁₇ClO
• 分子量: 260.763
• InChiKey: SQDWIPMYVBCJJX-INIZCTEOSA-N

物化性质

• 沸点：
  180-200 °C(Press: 0.5 Torr)
• 密度：
  1.106±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[(1S)-3-氯-1-苯基丙氧基]-2-甲基苯 以95%的产率得到
  参考文献：
  名称：

  BROWN, HERBERT C.

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯-1-苯基丙醇 在 吡啶 、 buffer pH 7 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 生成 1-[(1S)-3-氯-1-苯基丙氧基]-2-甲基苯
  参考文献：
  名称：

  An efficient route to enantiomerically pure antidepressants: tomoxetine, nisoxetine and fluoxetine

  摘要：

  Both enantiomers (R)- and (S)- 3-chloro- 1-phenyl- 1-propanol can be obtained conveniently by an efficient enzymatic resolution process. They can be converted via enantioconvergent routes into all enantiomers of the important antidepressants (R)- and (S)- Tomoxetine, Fluoxetine and Nisoxetine.

  DOI：

  10.1016/s0957-4166(00)80257-8

文献信息

• Chemoenzymatic synthesis of the non-tricyclic antidepressants Fluoxetine, Tomoxetine and Nisoxetine
  作者：Hui-Ling Liu、Bård Helge Hoff、Thorleif Anthonsen

  DOI：10.1039/b000846j

  日期：——

  3-Chloro-1-phenylpropan-1-ol and the corresponding butanoate, 3-chloro-1-phenyl-1-propyl butanoate, were kinetically resolved using lipase B from Candida antarctica catalysis by transesterification and hydrolysis respectively. The resulting chiral building blocks (S)- and (R)-3-chloro-1-phenylpropanol were converted into both enantiomers of the antidepressant drugs, Fluoxetine, Tomoxetine and Nisoxetine.

  使用来自南极念珠菌的脂肪酶B，通过酯交换和水解分别对3-氯-1-苯基丙醇及其相应的丁酸酯——3-氯-1-苯基-1-丙基丁酸酯进行了动力学拆分。得到的立体构建单元（S）-和（R）-3-氯-1-苯基丙醇被转化为抗抑郁药物氟西汀、托莫西汀和尼索西汀的两种对映体。
• Chiral synthesis via organoboranes. 18. Selective reductions. 43. Diisopinocampheylchloroborane as an excellent chiral reducing reagent for the synthesis of halo alcohols of high enantiomeric purity. A highly enantioselective synthesis of both optical isomers of Tomoxetine, Fluoxetine, and Nisoxetine
  作者：Morris Srebnik、P. V. Ramachandran、Herbert C. Brown

  DOI：10.1021/jo00248a005

  日期：1988.6
• Ader, U; Andersch, P; Berger, M, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 1, p. 145 - 150
  作者：Ader, U、Andersch, P、Berger, M、Goergens, U、Seemayer, R、Schneider, M

  DOI：——

  日期：——
• Iodinated tomoxetine derivatives as selective ligands for serotonin and norepinephrine uptake sites
  作者：Sumalee Chumpradit、Mei Ping Kung、Chitchanum Panyachotipun、Vichukorn Prapansiri、Catherine Foulon、Brian P. Brooks、Stephen A. Szabo、Shanaz Tejani-Butt、Alan Frazer、Hank F. Kung

  DOI：10.1021/jm00101a029

  日期：1992.11

  In order to develop selective radioactive ligands for the study of presynaptic monoamine uptake sites, iodinated derivatives of tomoxetine were synthesized and evaluated in radioligand binding assays. Iodotomoxetine derivatives showed high affinity for serotonin (5-HT) uptake sites using a rat cortical membrane preparation. Compound 1R,(R)-(-)-N-methyl-3-(4-iodo-2-methylphenoxy)-3-phenylpropanamine, was the most potent and showed high stereoselectivity for 5-HT uptake sites (K(i), R isomer = 0.65 nM, S isomer = 13.9 nM). Changing the position of the methyl group or eliminating the methyl group at the phenoxy ring resulted in a loss of stereoselectivity. Substitution of the methyl group of tomoxetine with iodine gave the R and S isomers of N-methyl-3-(2-iodophenoxy)-3-phenylpropanamine 4R and 4S. These compounds displayed stereoselectivity for the norepinephrine (NE) (K(i) values = 0.24 and 9.35 nM for R and S isomers, respectively). The in vitro binding data suggest that 1R and 4R are potential radioiodinated ligands for pharmacological studies of 5-HT and NE uptake sites, respectively.
• BROWN, H. C.
  作者：BROWN, H. C.

  DOI：——

  日期：——