(2S,4S,5S)-4-methyl-2-phenyl-5-trifluoromethyl-1,3-dioxolane | 507476-10-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4S,5S)-4-methyl-2-phenyl-5-trifluoromethyl-1,3-dioxolane
• 英文别名: 1,3-Dioxolane, 4-methyl-2-phenyl-5-(trifluoromethyl)-, (2S,4S,5S)-；(2S,4S,5S)-4-methyl-2-phenyl-5-(trifluoromethyl)-1,3-dioxolane
• CAS: 507476-10-0
• 化学式: C₁₁H₁₁F₃O₂
• 分子量: 232.202
• InChiKey: KAQGBFRZHRUZCC-HGNGGELXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S,5S)-4-methyl-2-phenyl-5-trifluoromethyl-1,3-dioxolane 在 三乙基硅烷 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以95%的产率得到(2S,3S)-3-benzyloxy-1,1,1-trifluorobutan-2-ol
  参考文献：
  名称：

  Regio- and diastereoselectivity in TiCl4-promoted reduction of 2-aryl-substituted cis-4-methyl-5-trifluoromethyl-1,3-dioxolanes

  摘要：

  TiCl4-mediated reduction of both syn- and anti-(4S,5S)-2-aryl-4-methyl-5-trifluoromethyl-1,3-dioxolanes with Et3SiD furnished monodeuterated hydroxy ethers resulting from the same regio- and stereoselective C-O bond cleavage (yields >80%; 82-92% de). Deuteride addition to the benzylidene acetal and removal of the alkyl moiety from the reaction product gave (R)-(alpha-H-2)benzy] alcohol (90% ee), thus suggesting a new route to chiral 1-deuteriobenzyl alcohols. A mechanistic rationale is proposed and supported by theoretical calculations. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00687-0
• 作为产物：
  描述：

  苯甲醛 、 (2S,3S)-1,1,1-trifluorobutane-2,3-diol 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以55%的产率得到(2S,4S,5S)-4-methyl-2-phenyl-5-trifluoromethyl-1,3-dioxolane
  参考文献：
  名称：

  Regio- and diastereoselectivity in TiCl4-promoted reduction of 2-aryl-substituted cis-4-methyl-5-trifluoromethyl-1,3-dioxolanes

  摘要：

  TiCl4-mediated reduction of both syn- and anti-(4S,5S)-2-aryl-4-methyl-5-trifluoromethyl-1,3-dioxolanes with Et3SiD furnished monodeuterated hydroxy ethers resulting from the same regio- and stereoselective C-O bond cleavage (yields >80%; 82-92% de). Deuteride addition to the benzylidene acetal and removal of the alkyl moiety from the reaction product gave (R)-(alpha-H-2)benzy] alcohol (90% ee), thus suggesting a new route to chiral 1-deuteriobenzyl alcohols. A mechanistic rationale is proposed and supported by theoretical calculations. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00687-0

文献信息

• Evidence for a nucleophilic anti-attack on the cleaved C(2)–oxygen bond in Cl2AlH-catalyzed ring-opening of 2-substituted 1,3-dioxolanes
  作者：Carlo F. Morelli、Arianna Fornili、Maurizio Sironi、Lavinia Durì、Giovanna Speranza、Paolo Manitto

  DOI：10.1016/j.tetlet.2005.01.108

  日期：2005.3

  cis-4-methyl-5-trifluoromethyl-1,3-dioxolanes was found to occur with regioselective cleavage of the O1–C2 bond by attack of the aluminum hydride from the direction anti to the departing oxygen. This stereochemical outcome, which appears to be unprecedented in the reductive cleavage of chiral acetals by aluminum reagents, is interpreted on the basis of theoretical calculations.

  发现Cl 2 AlH介导的2-取代的顺式-4-甲基-5-三氟甲基-1,3-二氧戊环的开环是由于氢化铝从一个方向进攻而导致的O1-C2键的区域选择性裂解而发生的。抗离去的氧气。在理论计算的基础上解释了这种立体化学结果，这在铝试剂对手性乙缩醛的还原裂解中似乎是空前的。
• Regio- and diastereoselectivity in TiCl4-promoted reduction of 2-aryl-substituted cis-4-methyl-5-trifluoromethyl-1,3-dioxolanes
  作者：Carlo F. Morelli、Arianna Fornili、Maurizio Sironi、Lavinia Durı̀、Giovanna Speranza、Paolo Manitto

  DOI：10.1016/s0957-4166(02)00687-0

  日期：2002.11

  TiCl4-mediated reduction of both syn- and anti-(4S,5S)-2-aryl-4-methyl-5-trifluoromethyl-1,3-dioxolanes with Et3SiD furnished monodeuterated hydroxy ethers resulting from the same regio- and stereoselective C-O bond cleavage (yields >80%; 82-92% de). Deuteride addition to the benzylidene acetal and removal of the alkyl moiety from the reaction product gave (R)-(alpha-H-2)benzy] alcohol (90% ee), thus suggesting a new route to chiral 1-deuteriobenzyl alcohols. A mechanistic rationale is proposed and supported by theoretical calculations. (C) 2002 Elsevier Science Ltd. All rights reserved.