3-iodo-1-propynyl(trimethyl)silane | 78199-88-9

• 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: 3-iodo-1-propynyl(trimethyl)silane
• 英文别名: 3-Iodo-1-trimethylsilylpropyne；3-iodoprop-1-ynyl(trimethyl)silane
• CAS: 78199-88-9
• 化学式: C₆H₁₁ISi
• 分子量: 238.143
• InChiKey: GEWOCRSOOHMPED-UHFFFAOYSA-N

物化性质

• 沸点：
  42 °C(Press: 2 Torr)
• 密度：
  1.4465 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3-iodo-1-propynyl(trimethyl)silane 生成 炔丙基碘化物
  参考文献：
  名称：

  Rh(I)-catalyzed Pauson–Khand reaction of 1-phenylsulfonyl-1,2-octadien-7-yne derivatives

  摘要：

  The Rh(I)-catalyzed PKR of 1-phenylsulfonyl- 1,2-octadien-7-ynes and their aza derivatives exclusively produced the corresponding 9-phenylsulfonylbicyclo[4.3.0]nona-1,6-dien-8-ones and no 4-(phenylsulfonylmethylidene)bicyclo [3.3. 0]oct-1-en-3-ones could be detected. Thus, the ring-closing pattern was found to be the same as those of the previously reported 3-phenylsulfonyl-1,2-octadien-7-yne derivatives. However, the formation of 4-(phenylsulfonylmethylidene)-7-oxabicyclo[3.3.0]oct-1-en-3-ones was observed as a minor product when the 5-oxa congeners were used. In addition, a larger ring-sized product, 10-phenylsulfonyl-5-azabicyclo[5.3.0]deca-1,7-dien-9-one derivative, was obtained from the 6-aza derivative of 1-phenylsulfonyl-1,2-nonadien-8-yne. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.005
• 作为产物：
  描述：

  (3-chloro-1-propynyl)trimethylsilane 在 sodium ethanolate 、 potassium iodide 、 苯甲酰硝基甲烷 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以22%的产率得到3-iodo-1-propynyl(trimethyl)silane
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1015546623846

文献信息

• Enantioselective assembly of the benzo[d]xanthene tetracyclic core of anti-influenza active natural products
  作者：Duc Tran Ngoc、Martin Albicker、Lorenz Schneider、Nicolai Cramer

  DOI：10.1039/c002011g

  日期：——

  A combination of an enantioselective conjugate addition/trapping sequence and a ruthenium(III)-catalyzed domino cyclization provides a concise access to benzo[d]xanthenes found in several anti-influenza active sesquiterpene natural products.

  一种结合了对映选择性共轭加成/捕捉序列与钌(III)催化多米诺环化的方法，为从几种抗流感活性倍半萜天然产物中发现的苯并[d]咕吨酮类化合物提供了简明的合成途径。
• REACTION OF PROPARGYL BROMIDE AND TRIMETHYLSILYLPROPARGYL IODIDE WITH METALLIC TIN, ALUMINUM, AND ALDEHYDES OR KETONES. SELECTIVE SYNTHESIS OF β-ACETYLENE, β-TRIMETHYLSILYLACETYLENE, AND α-TRIMETHYLSILYLALLENE ALCOHOLS
  作者：Junzo Nokami、Takashi Tamaoka、Tadao Koguchi、Rokuro Okawara

  DOI：10.1246/cl.1984.1939

  日期：1984.11.5

  β-Acetylenic and α-allenic alcohols were synthesized selectively by the reaction of aldehydes and ketones with organotin compounds prepared by treatment of propargyl bromide or trimethylsilylpropargyl iodide with metallic tin and aluminum in a suitable solvent.

  通过醛和酮与有机锡化合物反应选择性地合成β-乙炔和α-丙二烯醇，该有机锡化合物是通过在合适的溶剂中用金属锡和铝处理炔丙基溴或三甲基甲硅烷基炔丙基碘而制备的。
• A Direct and Stereocontrolled Route to Conjugated Enediynes
  作者：Graham B. Jones、Justin M. Wright、Gary W. Plourde、George Hynd、Robert S. Huber、Jude E. Mathews

  DOI：10.1021/ja993766b

  日期：2000.3.1

  A unified synthetic route to 3-hex-en-1,5-diynes, a key building block found in many of the enediyne antitumor agents and designed materials, was developed. The method, which relies on a carbenoid coupling-elimination strategy is tolerant of a wide range of functionalities, and was applied to the synthesis of a variety of linear and cyclic enediynes. Reaction parameters can be adjusted to control stereoselectivity

  开发了 3-hex-en-1,5-二炔的统一合成路线，这是在许多烯二炔抗肿瘤剂和设计材料中发现的关键组成部分。该方法依赖于类卡宾偶联消除策略，具有广泛的功能性，并被应用于各种线性和环状烯二炔的合成。可以调整反应参数以控制该过程的立体选择性，生产 E:Z 比为 1:12 至 >100:1 的线性烯二炔，在环状烯二炔的情况下，仅生成 Z C-9、C-10 或C-11 产品。该过程的主要特点是前体的现成可用性以及反应的温和性和效率。介绍了该过程在材料前体设计和烯二炔抗肿瘤剂制备中的应用。
• 1,1-Disilyl Alcohols as d1 Synthons: Harnessing the 1,2-Brook Rearrangement
  作者：Ian Fleming、Annabel J. Lawrence、Robert D. Richardson、David S. Surry、Mark C. West

  DOI：10.1002/1522-2675(200210)85:10<3349::aid-hlca3349>3.0.co;2-k

  日期：2002.10

  1,1-Disilyl alcohols like 6 give the silyl ethers like 9 on treatment with base and alkyl halides, in a reaction which may be formulated as the alkylation of the Brook-rearranged carbanion 8. The products can be oxidised to give ketones like 10, showing that this Brook-rearranging system supplies a controlled d1 synthon of the acyl anion class. The alcohols can be prepared from the acid chloride 12

  1,1-二甲硅烷醇（如 6）在用碱和卤代烷处理后得到甲硅烷基醚（如 9），反应可表述为布鲁克重排碳负离子 8 的烷基化反应。产物可被氧化得到酮（如 10） ，表明该布鲁克重排系统提供了酰基阴离子类的受控 d1 合成子。醇可以由酰氯12和二甲基(苯基)甲硅烷基锂制备，但中间体阴离子21不需要后处理；它可以直接用于烷基化步骤。
• Syntheses of isocarbacyclin by highly regioselective alkylation of allylic alcohols
  作者：Kiyoshi Bannai、Toshio Tanaka、Noriaki Okamura、Atsuo Hazato、Satoshi Sugiura、Kenji Manabe、Koji Tomimori、Yoshinori Kato、Seizi Kurozumi、Ryoji Noyori

  DOI：10.1016/s0040-4020(01)87859-5

  日期：1990.1

  Syntheses of isocarbacyclin (20) using highly regioselective alkylation of the new allylic alcohol intermediate 6 having an exocyclic double bond are described. The allylic alcohol 6 was prepared by (i) allylic rearrangement of the allylic alcohol 3 having an endocyclic double bond and (ii) reductive cyclization of γ-ethynyl aldehyde 11a which was synthesized from (R)-4-hydroxy-2- cyclopentenone derivative

  描述了使用具有环外双键的新的烯丙基醇中间体6的高度区域选择性烷基化来合成异碳环素（20）。烯丙基醇6是通过（i）具有环内双键的烯丙基醇3的烯丙基重排和（ii）由（R）-4-羟基-2-环戊烯酮衍生物合成的γ-乙炔醛11a的还原环化而制备的。1在5个步骤。通过使用Murahashi的方法实现了烯丙基醇6的γ-烷基化，从而导致异碳环素的高度区域选择性的形成（区域选择性为99％）。烯丙醇的α-烷基化3 还获得了构建异卡巴环素的方法。