3-(Trimethylsilyl)propargyl ethyl carbonate | 167275-01-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 3-(Trimethylsilyl)propargyl ethyl carbonate
• 英文别名: ethyl 3-(trimethylsilyl)prop-2-ynyl carbonate；Ethyl 3-trimethylsilylprop-2-ynyl carbonate
• CAS: 167275-01-6
• 化学式: C₉H₁₆O₃Si
• 分子量: 200.31
• InChiKey: UIOLKJVGRGCVJN-UHFFFAOYSA-N

物化性质

• 沸点：
  199.7±23.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(Trimethylsilyl)propargyl ethyl carbonate 在 吡啶 、 titanium(IV) isopropylate 、 异丙基溴化镁 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Highly efficient synthesis of alka-1,3-dien-2-yltitanium compounds from alka-2,3-dienyl carbonates. A new, practical synthesis of 1,3-dienes and 2-iodo-1,3-dienes

  摘要：

  Treatment of carbonates of alka-2,3-dien-1-ols 2 with (eta(2)-propene)Ti(O-i-Pr)(2) (I) resulted in oxidative addition to afford 1,3-dien-2-yltitanium compounds 3, which react readily with electrophiles such as H+, I-2 and aldehydes. The reaction with H+ and I-2 proceeds highly regioselectively, thus providing an efficient and practical method for synthesis of 1,3-dienes and 2-iodo-1,3-dienes. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02126-0
• 作为产物：
  描述：

  3-(tetrahydropyran-2-yloxy)-1-trimethylsilylprop-1-yne 在 吡啶 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 9.0h， 生成 3-(Trimethylsilyl)propargyl ethyl carbonate
  参考文献：
  名称：

  Palladium-Catalyzed Reductive Homocoupling Reaction of 3-Silylpropargyl Carbonates. New Entry into Allene-Yne Compounds

  摘要：

  DOI：

  10.1021/jo00119a052

文献信息

• Titanium/Palladium-Mediated Regioselective Propargylation of Ketones using Propargylic Carbonates as Pronucleophiles
  作者：Alba Millán、Luis Álvarez de Cienfuegos、Ana Martín-Lasanta、Araceli G. Campaña、Juan M. Cuerva

  DOI：10.1002/adsc.201000655

  日期：2011.1.10

  for the synthesis of homopropargylic alcohols using propargylic carbonates as pronucleophiles is reported. The reaction is based on a combination of transition metal (palladium) and radical chemistry (titanium). The reaction takes place with an excellent regioselectivity and tolerates a great degree of substitution of the starting propargylic carbonate, thus being an interesting tool in the context

  报道了使用炔丙基碳酸酯作为亲核试剂的高效合成炔丙醇的方案。该反应基于过渡金属（钯）和自由基化学（钛）的组合。该反应以优异的区域选择性进行，并且可以耐受起始炔丙基碳酸酯的很大程度的取代，因此在合成有机化学的背景下是令人感兴趣的工具。
• Highly selective addition reaction of organotitaniums with Garner's aldehyde. Easy preparation of optically active allylic, allenylic, homoallylic and homopropargylic alcohols
  作者：Christophe Delas、Sentaro Okamoto、Fumie Sato

  DOI：10.1016/s0040-4039(02)00783-9

  日期：2002.6

  Organotitanium complexes 3–5 prepared from a Ti(O-i-Pr)4/2/i-PrMgX reagent (2) and the corresponding unsaturated compounds reacted with Garner's aldehyde (1) to provide anti-addition products highly predominantly, thus allowing an easy access to a variety of optically active anti-1,2-aminoalcohol derivatives.

  有机钛络合物3 - 5从由Ti制备（O-我-Pr）4 /2 /我-PrMgX试剂（2）和相应的不饱和化合物与加纳的醛（反应1），以提供抗高度主要-addition产品，从而允许容易获得各种光学活性的抗-1,2-氨基醇衍生物。
• Electrophilic amination of racemic and non-racemic allenyltitaniums. One-pot synthesis of α-hydrazinoalkynes from propargylic alcohol derivatives
  作者：Duk Keun An、Koichiro Hirakawa、Sentaro Okamoto、Fumie Sato

  DOI：10.1016/s0040-4039(99)00584-5

  日期：1999.5

  a reagent and dialkyl azodicarboxylates gave α-hydrazinoalkynes in good yields. The reaction, which proceeded with up to 86% chiral transfer, thus has opened up a new route to optically active α-hydrazinoalkynes from the optically active propargylic compounds.

  用试剂和偶氮二羧酸二烷基酯连续处理炔丙基碳酸酯或磷酸酯，得到的α-肼基炔烃产率高。该反应进行至多86％的手性转移，因此开辟了从旋光的炔丙基化合物制备旋光的α-肼基炔烃的新途径。
• Palladium-Catalyzed Reductive Homocoupling Reaction of 3-Silylpropargyl Carbonates. New Entry into Allene-Yne Compounds
  作者：Sensuke Ogoshi、Shinji Nishiguchi、Ken Tsutsumi、Hideo Kurosawa

  DOI：10.1021/jo00119a052

  日期：1995.7
• Highly efficient synthesis of alka-1,3-dien-2-yltitanium compounds from alka-2,3-dienyl carbonates. A new, practical synthesis of 1,3-dienes and 2-iodo-1,3-dienes
  作者：Sentaro Okamoto、Hiroyoshi Sato、Fumie Sato

  DOI：10.1016/s0040-4039(96)02126-0

  日期：1996.12

  Treatment of carbonates of alka-2,3-dien-1-ols 2 with (eta(2)-propene)Ti(O-i-Pr)(2) (I) resulted in oxidative addition to afford 1,3-dien-2-yltitanium compounds 3, which react readily with electrophiles such as H+, I-2 and aldehydes. The reaction with H+ and I-2 proceeds highly regioselectively, thus providing an efficient and practical method for synthesis of 1,3-dienes and 2-iodo-1,3-dienes. Copyright (C) 1996 Elsevier Science Ltd.