(chloromethyl)(triphenyl)germane | 27259-63-8

• 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: (chloromethyl)(triphenyl)germane
• 英文别名: chloromethyl-triphenyl germane；Chlormethyl-triphenyl-german；(Chlormethyl)triphenylgerman；Triphenyl-chlormethyl-german；(Chloromethyl)triphenylgermane；chloromethyl(triphenyl)germane
• CAS: 27259-63-8
• 化学式: C₁₉H₁₇ClGe
• 分子量: 353.387
• InChiKey: HDBKOSQMSVSQFV-UHFFFAOYSA-N

物化性质

• 熔点：
  117.5-118.5 °C(Solv: ligroine (8032-32-4))
• 沸点：
  409.3±47.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (chloromethyl)(triphenyl)germane 、 sodium azide 以 further solvent(s) 为溶剂， 以63%的产率得到triphenylgermylmethylazide
  参考文献：
  名称：

  Syntheses and crystal structures of azafulleroid and aziridinofullerene bearing silyl or germyl benzene

  摘要：

  Addition of silyl and germylmethyl azides (1) to fullerene C-60 at 50 degrees C through [2+3] cycloaddition led to the formation of the triazoline adducts (2). Subsequently, heating 2 at 100 degrees C in the solid state, caused N-2 extrusion producing two different isomers, [5,6]-azafulleroid (3) and [6,6]-aziridinofullerene (4). The C-13 NMR spectrum of 3 had an absence of resonances in the aliphatic region for the fullerene C-60 cage, showing a fulleroid with CS symmetry. In contrast, 4 exhibited one sp(3) resonance in the aliphatic region for the fullerene C-60 cage, indicative of an aziridinofullerene with C-2V symmetry. However, MALDI-TOF mass characterization was hampered because ion peaks corresponding to the bis-adduct are detected in positive ion mode measurements, whereas the ion peaks [M-N-2] for 2a as well as [M] for 3a and 4a are observed in negative ion measurements. In an effort to obtain X-ray data, silyl and germylphenyl groups were introduced to form intermolecular complexes with fullerene C-60. The X-ray structures of 3c and 3d revealed a strong enhancement of homoconjugation in the bridged annulene moiety based on POAV analysis. The X-ray structures of 3c,d and 4c were confirmed with the detection of silyl and germylphenyl-C-60 interactions, similar to dimethoxyphenyl-C-60 interactions. (C) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.11.049
• 作为产物：
  描述：

  溴氯甲烷 、 三苯基溴化锗 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到(chloromethyl)(triphenyl)germane
  参考文献：
  名称：

  通过氯硅烷的低温反应合成四氯呋喃并原位生成的（氯甲基）锂

  摘要：

  The reaction between chlorosilanes and (chloromethyl)lithium, generated in situ from bromochloromethane and n-butyllithium, was used to synthesize (chloromethyl)silanes. The method is applicable to a wide variety of chlorosilanes and is particularly useful for silanes that contain such reactive bonds as Si-Si, Si-H, Si-vinyl, and Si-allyl. The corresponding (chloromethyl)silanes are generally prepared in high yield. The method may be extended successfully to bromomethylation and iodomethylation of chlorosilanes, and also to the chloromethylation of the other group 14 element (Ge, Sn, and Pb) halides.

  DOI：

  10.1021/om00052a049

文献信息

• Homologation of halostannanes with carbenoids: a convenient and straightforward one-step access to α-functionalized organotin reagents
  作者：Saad Touqeer、Laura Castoldi、Thierry Langer、Wolfgang Holzer、Vittorio Pace

  DOI：10.1039/c8cc04786c

  日期：——

  A direct, single synthetic homologative transformation of halostannanes into mono- or di-substituted methyl analogues is documented. Critical for the success of the operation is the excellent nucleophilicity of carbenoid-like methyllithium reagents (LiCHXY, X, Y = halogen, OR, and CN): by simply individuating the reagents’ substitution pattern, the desired functionalized fragment is delivered to the

  文献记载了卤代烷烃直接，单一的合成同源性转化为单取代或二取代的甲基类似物。操作成功的关键是类胡萝卜素样甲基锂试剂（LiCHXY，X，Y =卤素，OR和CN）的优异亲核性：通过简单地区分试剂的取代方式，所需的官能化片段将被递送至亲电子试剂。在类似的卤代compounds化合物的情况下，也证明了该方案的广泛范围。还讨论了亲核试剂的串联同源猝灭和α-氯烯丙基锂的使用。
• The Reactions of Triphenylgermyllithium, Triphenylgermylpotassium and Triphenylgermane with Some Olefins
  作者：Henry Gilman、Clare W. Gerow

  DOI：10.1021/ja01559a027

  日期：1957.1
• Syntheses and crystal structures of azafulleroid and aziridinofullerene bearing silyl or germyl benzene
  作者：Houjin Hachiya、Toshiyuki Kakuta、Makoto Takami、Yoshio Kabe

  DOI：10.1016/j.jorganchem.2008.11.049

  日期：2009.3

  Addition of silyl and germylmethyl azides (1) to fullerene C-60 at 50 degrees C through [2+3] cycloaddition led to the formation of the triazoline adducts (2). Subsequently, heating 2 at 100 degrees C in the solid state, caused N-2 extrusion producing two different isomers, [5,6]-azafulleroid (3) and [6,6]-aziridinofullerene (4). The C-13 NMR spectrum of 3 had an absence of resonances in the aliphatic region for the fullerene C-60 cage, showing a fulleroid with CS symmetry. In contrast, 4 exhibited one sp(3) resonance in the aliphatic region for the fullerene C-60 cage, indicative of an aziridinofullerene with C-2V symmetry. However, MALDI-TOF mass characterization was hampered because ion peaks corresponding to the bis-adduct are detected in positive ion mode measurements, whereas the ion peaks [M-N-2] for 2a as well as [M] for 3a and 4a are observed in negative ion measurements. In an effort to obtain X-ray data, silyl and germylphenyl groups were introduced to form intermolecular complexes with fullerene C-60. The X-ray structures of 3c and 3d revealed a strong enhancement of homoconjugation in the bridged annulene moiety based on POAV analysis. The X-ray structures of 3c,d and 4c were confirmed with the detection of silyl and germylphenyl-C-60 interactions, similar to dimethoxyphenyl-C-60 interactions. (C) 2008 Elsevier B. V. All rights reserved.
• Synthesis of (chloromethyl)silanes by the low-temperature reaction of chlorosilanes and in situ generated (chloromethyl)lithium in tetrahydrofuran
  作者：Toshiaki Kobayashi、Keith H. Pannell

  DOI：10.1021/om00052a049

  日期：1991.6

  The reaction between chlorosilanes and (chloromethyl)lithium, generated in situ from bromochloromethane and n-butyllithium, was used to synthesize (chloromethyl)silanes. The method is applicable to a wide variety of chlorosilanes and is particularly useful for silanes that contain such reactive bonds as Si-Si, Si-H, Si-vinyl, and Si-allyl. The corresponding (chloromethyl)silanes are generally prepared in high yield. The method may be extended successfully to bromomethylation and iodomethylation of chlorosilanes, and also to the chloromethylation of the other group 14 element (Ge, Sn, and Pb) halides.