1-(o-carboranyl)benzyl alcohol | 20539-32-6

• 英文名称: 1-(o-carboranyl)benzyl alcohol
• 英文别名: o-carboranyl(phenyl)methanol；1-(CH(C6H5)OH)-1.2-C2B10H11；o-carboranylbenzyl alcohol
• CAS: 20539-32-6；257889-14-8
• 化学式: C₉H₁₈B₁₀O
• 分子量: 250.351
• InChiKey: VTKDQVLITVFLJX-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1-(o-carboranyl)benzyl alcohol 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以90%的产率得到methoxy(phenyl)methyl-o-carborane
  参考文献：
  名称：

  Chiral organotin complexes stabilized by C,N-chelating oxazolinyl-o-carboranes

  摘要：

  A series of chiral organotin halides containing 2-(4-R)-oxazolinyl-o-carboranes (R = i-propyl 1, t-butyl 2; Cab(Oxa)) was prepared from o-carborane with a chiral oxazoline auxiliary. X-ray structural analysis of the representative chiral organotin halide, [2-(4-i-propyl)-oxazolinyl-o-carboranyl]SnMe(2)Br (4), revealed the formation of a stable penta-coordinated tin center due to a N -> Sn interaction. Similar O -> Sn assisted intramolecular penta-coordinated tin complexes (9 and 10) were prepared from methoxy-o-carborane ligands, MeOCH(Z)-o-carborane (Z = H 7, Ph 8; Cab(OMe)), respectively, and a rigid o-carboranyl backbone provided the basic skeleton for the facile formation of organotin complexes. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.10.030
• 作为产物：
  描述：

  1,2-dicarba-closo-dodecaborane(12) 、 苯甲醛 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到1-(o-carboranyl)benzyl alcohol
  参考文献：
  名称：

  四丁基氟化铵促进邻碳硼烷的新反应：醛和酮的分子间和分子内加成以及通过烯醛和烯酮的环化

  摘要：

  在室温下，在四丁基氟化铵水溶液（TBAF；3 当量）的存在下，邻碳硼烷 (1) 向醛 2 的加成非常顺利，以高产率得到相应的甲醇 3。将 TBAF 介导的反应应用于邻碳硼醛和酮 4 的分子内环加成反应，并以良好到高的产率获得了相应的五元、六元和七元碳环。此外，在 TBAF 存在下，邻碳硼烷（双阴离子 C2 合成子）与 α,β-不饱和醛和酮（双阴离子 C3 合成子）之间的 [3 + 2] 环化进行得非常顺利，得到相应的五元碳环到高产量。详细的机理研究表明 [3 + 2] 环化是通过动力学控制的 1,2-加成和热力学控制的 1 进行的，

  DOI：

  10.1021/ja973832e

文献信息

• Stanko, V. I.; Brattsev, V. A.; Al'perovich, N. E., Zhurnal Obshchei Khimii, 1968, vol. 38, p. 1015 - 1020
  作者：Stanko, V. I.、Brattsev, V. A.、Al'perovich, N. E.、Titova, N. S.

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.12, 4.6.1.1, page 1 - 23
  作者：

  DOI：——

  日期：——
• Synthetic utility of o-carborane: novel protective group for aldehydes and ketones
  作者：Hiroyuki Nakamura、Kouichi Aoyagi、Yoshinori Yamamoto

  DOI：10.1016/s0022-328x(98)00922-x

  日期：1999.2

  o-Carborane acts as a novel protective group of carbonyl compounds. The reaction of lithiocarborane 2, which was prepared in an essentially quantitative yield from o-carborane and n-butyllithium, with aldehydes or ketones 1 gave the corresponding addition products, o-carboranyl methanol derivatives 3, in high yields. Cleavage of o-carborane from 3 was carried out by treating 3 with catalytic amounts of KOH in THF/H2O (100/1), giving the corresponding aldehydes or ketones in good to high yields along with recovered o-carborane. Accordingly, o-carborane may be utilized as a protective group stable under protic and Lewis acid conditions. Selective alkylation of an ester group, selective reduction of an ester, and selective alkylation of a ketone in the presence of an aldehyde are accomplished by using o-carborane protective groups. (C) 1999 Elsevier Science S.A. All rights reserved.
• Electronic Effects of Icosahedral Carboranes. Retentive Solvolysis of (1,2-Dicarba-<i>c</i><i>loso</i>-dodecaboran-1-yl)benzyl <i>p</i>-Toluenesulfonates
  作者：Yasuyuki Endo、Takehiko Sawabe、Yoshiyuki Taoda

  DOI：10.1021/ja993517n

  日期：2000.1.1