(2-hydroxy-2-phenyl)ethyl-(2-pyridyl)dimethylsilane

• 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: (2-hydroxy-2-phenyl)ethyl-(2-pyridyl)dimethylsilane
• 英文别名: 2-pyridyldimethyl(2-hydroxy-2-phenylethyl)silane；dimethyl(2-hydroxy-2-phenylethyl)(pyridin-2-yl)silane；dimethyl(2-hydroxy-2-phenylethyl1)(2-pyridyl)silane；Dimethyl(2-hydroxy-2-phenylethyl)(2-pyridyl)silane；2-[dimethyl(pyridin-2-yl)silyl]-1-phenylethanol
• 化学式: C₁₅H₁₉NOSi
• 分子量: 257.407
• InChiKey: UBXIDCLAKWTFSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-hydroxy-2-phenyl)ethyl-(2-pyridyl)dimethylsilane 在 potassium fluoride 、 双氧水 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以96%的产率得到苯基乙二醇
  参考文献：
  名称：

  (2-Pyridyldimethylsilyl)methyl lithium as a novel hydroxymethylating reagent

  摘要：

  (2-吡啶基二甲基硅基)甲基锂被发现能与有机溴化物、醛、酮和氢硅烷反应，产率良好至优异。所得的加成物进一步用H₂O₂/KF氧化，以优异的产率生成相应的醇。因此，这一两步转化提供了一种高效的羟甲基化方法。（C）1999 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4039(99)01028-x
• 作为产物：
  描述：

  苯甲醛 、 2-三甲基硅基吡啶 在 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 1.5h， 以85%的产率得到(2-hydroxy-2-phenyl)ethyl-(2-pyridyl)dimethylsilane
  参考文献：
  名称：

  (2-Pyridyldimethylsilyl)methyl lithium as a novel hydroxymethylating reagent

  摘要：

  (2-吡啶基二甲基硅基)甲基锂被发现能与有机溴化物、醛、酮和氢硅烷反应，产率良好至优异。所得的加成物进一步用H₂O₂/KF氧化，以优异的产率生成相应的醇。因此，这一两步转化提供了一种高效的羟甲基化方法。（C）1999 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4039(99)01028-x

文献信息

• (2-Pyridyldimethylsilyl)methyl lithium as a novel hydroxymethylating reagent
  作者：Kenichiro Itami、Koichi Mitsudo、Jun-ichi Yoshida

  DOI：10.1016/s0040-4039(99)01028-x

  日期：1999.7

  (2-Pyridyldimethylsilyl)methyl lithium was found to react with organic bromides, aldehydes, ketones, and hydrosilanes in good to excellent yields. The resultant adducts were further oxidized with H2O2/KF to give the corresponding alcohols in excellent yields. Thus, this two-step transformation provides an efficient method for hydroxymethylation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (2-吡啶基二甲基硅基)甲基锂被发现能与有机溴化物、醛、酮和氢硅烷反应，产率良好至优异。所得的加成物进一步用H₂O₂/KF氧化，以优异的产率生成相应的醇。因此，这一两步转化提供了一种高效的羟甲基化方法。（C）1999 Elsevier Science Ltd. 保留所有权利。
• 2-pyridylsilane, processes for producing and using the same
  申请人：SUMITOMO CHEMICAL CO., LTD.

  公开号：US20030139600A1

  公开（公告）日：2003-07-24

  The present invention provides a compound which can be purified by conventional acid/base extraction. There is disclosed 2-pyridylsilane of formula (1): 1 wherein R 1 represents an alkyl group, etc, R 2 and R 3 represent an alkyl group, an alkoxy group, etc., R 4 , R 5 , R 6 and R 7 represent a hydrogen atom, a halogen atom, an alkyl group, etc.

  本发明提供了一种可通过传统的酸/碱萃取法纯化的化合物。公开了式（1）的2-吡啶基硅烷：其中R1表示烷基等，R2和R3表示烷基、烷氧基等，R4、R5、R6和R7表示氢原子、卤原子、烷基等。
• 2-Pyridylsilane, processes for producing and using the same
  申请人：Sumitomo Chemical Co., Ltd.

  公开号：US20020165397A1

  公开（公告）日：2002-11-07

  The present invention provides a compound which can be purified by conventional acid/base extraction. There is disclosed 2-pyridylsilane of formula (1): 1 wherein R 1 represents an alkyl group, etc, R 2 and R 3 represent an alkyl group, an alkoxy group, etc, R 4 , R 5 , R 6 and R 7 represent a hydrogen atom, a halogen atom, an alkyl group, etc.

  本发明提供了一种可通过传统的酸/碱萃取法纯化的化合物。其中披露了式（1）的2-吡啶基硅烷：1，其中R1代表烷基，等等，R2和R3代表烷基，烷氧基等，R4、R5、R6和R7代表氢原子，卤素原子，烷基等。
• 2-Pyridysilane, processes for producing and using the same
  申请人：Sumitomo Chemical Company, Limited

  公开号：US06531602B2

  公开（公告）日：2003-03-11

  The present invention provides a compound which can be purified by conventional acid/base extraction. There is disclosed 2-pyridylsilane of formula (1): wherein R1 represents an alkyl group, etc, R2 and R3 represent an alkyl group, an alkoxy group, etc, R4, R5, R6 and R7 represent a hydrogen atom, a halogen atom, an alkyl group, etc.

  本发明提供了一种可以通过常规酸/碱萃取法纯化的化合物。公开了式（1）的2-吡啶基硅烷：其中R1代表烷基等，R2和R3代表烷基，烷氧基等，R4、R5、R6和R7代表氢原子，卤素原子，烷基等。
• Pyridyl Group Assisted Deprotonation of a Methyl Group on Silicon:  Complex Induced Proximity Effect and Novel Hydroxymethylation
  作者：Kenichiro Itami、Toshiyuki Kamei、Koichi Mitsudo、Toshiki Nokami、Jun-ichi Yoshida

  DOI：10.1021/jo015528g

  日期：2001.6.1

  A novel methodology for the deprotonation of a methyl group on silicon has been developed. This newly developed cr-lithiation protocol is based on the intramolecular pyridyl group coordination to stabilize the a-silyl carbanion together with the inherent silicon a effect. It was found that the deprotonation (t-BuLi/Et(2)O/-78 degreesC) occurs with 2-pyridyltrimethylsilane but not with other related silanes such as phenyltrimethylsilane, 3-pyridyltrimethylsilane, and 4-pyridyltrimethylsilane. It seems that this deprotonation proceeded through the agency of the complex-induced proximity effect (CIPE) of a 2-pyridyl group on silicon. (1)H NMR analysis of (2-pyridyldimethylsilyl)methyllithium revealed the intramolecular coordination of a pyridyl group to lithium. ( 2-Pyridyldimethylsilyl)-methyllithium was found to react with chlorosilanes, hydrosilanes, chlorostannanes, bromine, iodine, organic bromides, aldehydes, and ketones in good to excellent yields. The resultant adducts were further oxidized with H(2)O(2)/KF to give the corresponding alcohols in excellent yields. Thus, this two-step transformation provides an efficient method for the nucleophilic hydroxymethylation.