(2S,3R)-1-<(tert-butyldiphenylsilyl)oxy>-2-methylhex-5-en-3-ol | 106296-61-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3R)-1-<(tert-butyldiphenylsilyl)oxy>-2-methylhex-5-en-3-ol
• 英文别名: (2S,3R)-1-(tert-butyldiphenylsilyloxy)-2-methylhex-5-en-3-ol；(2S,3R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methylhex-5-en-3-ol；(2S,3R)-1-[tert-butyl(diphenyl)silyl]oxy-2-methylhex-5-en-3-ol
• CAS: 106296-61-1
• 化学式: C₂₃H₃₂O₂Si
• 分子量: 368.591
• InChiKey: JKUPTISZYOJMLN-SIKLNZKXSA-N

物化性质

• 沸点：
  439.7±45.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1-<(tert-butyldiphenylsilyl)oxy>-2-methylhex-5-en-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R)-2-methylhex-5-en-2,3-diol
  参考文献：
  名称：

  Asymmetric synthesis using tartrate ester modified allylboronates. 2. Single and double asymmetric reactions with alkoxy-substituted aldehydes

  摘要：

  DOI：

  10.1021/jo00300a032
• 作为产物：
  描述：

  (2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal 、 diisopropyl (S,S)-tartrate allylboronate 生成 (2S,3R)-1-<(tert-butyldiphenylsilyl)oxy>-2-methylhex-5-en-3-ol
  参考文献：
  名称：

  ROUSH, WILLIAM R.;HOONG, LEE K.;PALMER, MICHELLE A. J.;STRAUB, JULIE A.;P+, J. ORG. CHEM., 55,(1990) N3, C. 4117-4126

  摘要：

  DOI：

文献信息

• Iridium-Catalyzed Allylation of Chiral β-Stereogenic Alcohols: Bypassing Discrete Formation of Epimerizable Aldehydes
  作者：Daniel C. Schmitt、Anne-Marie R. Dechert-Schmitt、Michael J. Krische

  DOI：10.1021/ol3030692

  日期：2012.12.21

  4-dinitro-C,O-benzoate complex modified by (R)- or (S)-Cl,MeO-BIPHEP promotes the transfer hydrogenative coupling of allyl acetate to β-stereogenic alcohols with good to excellent levels of catalyst-directed diastereoselectivity to furnish homoallylic alcohols. Remote electronic effects of the C,O-benzoate of the catalyst play a critical role in suppressing epimerization of the transient α-stereogenic

  ( R )-或( S )-Cl,MeO-BIPHEP修饰的环金属化π-烯丙基3,4-二硝基-C,O-苯甲酸配合物促进乙酸烯丙酯向β-立体醇的转移加氢偶联，具有良好到优异的性能提供高烯丙醇的催化剂导向的非对映选择性水平。催化剂的C,O-苯甲酸酯的远程电子效应在抑制瞬态 α-立体醛的差向异构化方面起着关键作用。
• SYNTHESIS OF (+)-B-ALLYLDIISOPINOCAMPHEYLBORANE AND ITS REACTION WITH ALDEHYDES
  作者：Sun, Huikai、Roush, William R.

  DOI：10.15227/orgsyn.088.0087

  日期：——
• N,N'-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide: An Improved Chiral Auxiliary for the Asymmetric Allylboration Reaction
  作者：William R. Roush、Paul T. Grover

  DOI：10.1021/jo00117a036

  日期：1995.6

  N,N-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide (8), synthesized by a simple four-step sequence from ethylenediamine and benzylidenetartaric acid, was designed in anticipation that the derived allylboronates 9-11 would display enhanced reactivity owing to the inductive effect of the N-trifluoroethyl substituents that would increase the Lewis acidity of the boron atom of the B-allyl-1,3,2-dioxaborolanes. Reagents 9-11 were synthesized by transesterification of 8 with the crystalline and easily purified allylboronate diethanolamine complexes 13, 19, and 25. Allylboronate 9 is ca. 100-fold more reactive than 6 and is also substantially more useful than the previously reported allyboronate 4, which suffers from very poor solubility in toluene at -78 degrees C. Most importantly, allylboronates 9-11 are significantly more enantioselective than the parent tartrate allylboronates 1-3 and rank among the most highly enantioselective allylboron reagents yet reported. Reactions of 9-11 with aldehydes are performed in THF at- -78 or -55 degrees C for 5-12 h periods. The enantioselectivity realized in reactions with achiral aldehydes is 92-95% ee (Table 2), and excellent diastereoselectivity is achieved in double asymmetric reactions with chiral aldehydes 15a, 15b, and 33 (Tables 3 and 4). For example, 16 and 28 are now available with a minimum selectivity of 92% from reactions of 15a and 15b with allylboronate 9, while the crotylboration products 29, 30, and 31 are available with a minimum selectivity of 90% (usually greater than or equal to 95%) from reactions of 15a and 15b with crotylboronates 10 and 11; the fourth isomer, 32a, is available with 83% selectivity. Chiral reagents 9-11 thus appear well suited for application to complex problems in organic synthesis.
• ROUSH W. R.; PALKOWITZ A. D.; PALMER M. J., J. ORG. CHEM., 52,(1987) N 2, 316-318
  作者：ROUSH W. R.、 PALKOWITZ A. D.、 PALMER M. J.

  DOI：——

  日期：——