(S)-(+)-tert-Butyl(2-iodo-1-methylethoxy)dimethylsilane | 117289-79-9

• 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: (S)-(+)-tert-Butyl(2-iodo-1-methylethoxy)dimethylsilane
• 英文别名: (S)-tert-butyl((1-iodopropan-2-yl)oxy)dimethylsilane；(S)-2-(tert-butyldimethylsilyloxy)propyl iodide；(S)-2-t-butyldimethylsiloxy-1-iodopropane；(S)-tert-butyl-(2-iodo-1-methyl-ethoxy)-dimethyl-silane；tert-butyl-[(2S)-1-iodopropan-2-yl]oxy-dimethylsilane
• CAS: 117289-79-9
• 化学式: C₉H₂₁IOSi
• 分子量: 300.255
• InChiKey: YJKBMRIXPNAHBN-QMMMGPOBSA-N

物化性质

• 沸点：
  225.5±23.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-(+)-tert-Butyl(2-iodo-1-methylethoxy)dimethylsilane 在 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 (E)-(2R,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoic acid
  参考文献：
  名称：

  jaspamide（jasplakinolide）和geodiamolide A和B的全合成- 1的（2立体选择性合成，4 ，6 ，8 ）-8-羟基-2,4,6-三甲基-4- nonenoicic酸1

  摘要：

  通过非对映选择性烷基化制备手性醛7，随后1,2-添加异丙烯基溴化镁得到烯丙基醇8和10的混合物（68:32），通过再循环MPLC将其分离。这些醇的丙酸酯的克莱森重排在烯醇盐几何形状的控制下最终产生羟基壬烯酸12b。

  DOI：

  10.1016/s0040-4039(00)80273-7
• 作为产物：
  描述：

  (S)-2-((tert-butyldimethylsilyl)oxy)propan-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 生成 (S)-(+)-tert-Butyl(2-iodo-1-methylethoxy)dimethylsilane
  参考文献：
  名称：

  叠氮化物和不对称炔烃的区域选择性分子内偶极环加成反应

  摘要：

  对映体富集的烯丙基硅烷用于与醛和甲硅烷基醚的三组分炔丙基化反应，以形成含有嵌入叠氮化物的顺-均炔基醚。然后这些材料经历热诱导的分子内 1,3-偶极环加成反应，产生含有 1,2,3-三唑的独特稠环系统。改变反应的所有三个组分的能力允许方便地获得含有显着结构和立体化学变化的化合物。

  DOI：

  10.1021/ol902681t

文献信息

• Heterocyclic inhibitors of MEK and methods of use thereof
  申请人：Wallace Eli

  公开号：US20050054701A1

  公开（公告）日：2005-03-10

  Disclosed are compounds of the Formula I and pharmaceutically acceptable salts and prodrugs thereof, wherein R 1 , R 2 , R 7 , R 8 , R 9 and R 10 , W and Y are as defined in the specification. Such compounds are MEK inhibitors and useful in the treatment of hyperproliferative diseases, such as cancer and inflammation, in mammals. Also disclosed are methods of using such compounds in the treatment of hyperproliferative diseases in mammals and pharmaceutical compositions containing such compounds.

  揭示了Formula I的化合物及其药用盐和前药，其中R1、R2、R7、R8、R9和R10、W和Y如规范中所定义。这些化合物是MEK抑制剂，在哺乳动物中用于治疗高增殖性疾病，如癌症和炎症。还公开了在哺乳动物中使用这些化合物治疗高增殖性疾病的方法以及含有这些化合物的药物组合物。
• Hydrosulfonylation Reaction with Arenesulfonyl Chlorides and Tetrahydrofuran: Conversion of Terminal Alkynes into Cyclopentylmethyl Sulfones
  作者：Christian Simon Gloor、Fabrice Dénès、Philippe Renaud

  DOI：10.1002/anie.201707791

  日期：2017.10.16

  chain reaction to convert terminal alkynes into arenesulfonylmethylcyclopentanes is described. The reaction involves a radical addition–translocation–cyclization process and necessitates solely the use of readily available arenesulfonyl chlorides in tetrahydrofuran. Interestingly, this radical‐mediated C−H activation process took place with a high level of retention of configuration when an enantiomerically

  描述了将末端炔烃转化为芳烃磺酰基甲基环戊烷的有效且简单的自由基链反应。该反应涉及自由基加成-易位-环化过程，仅需要在四氢呋喃中使用容易获得的芳烃磺酰氯。有趣的是，当使用对映体纯的起始原料时，这种自由基介导的CH活化过程在高度保留构型的情况下进行。
• Kraft, Philip; Tochtermann, Werner, Liebigs Annalen, 1995, # 8, p. 1409 - 1414
  作者：Kraft, Philip、Tochtermann, Werner

  DOI：——

  日期：——
• Practical Syntheses of Enantiomerically Enriched γ-Lactones and γ-Hydroxy Ketones by the Alkylation of Pseudoephedrine Amides with Epoxides and Their Derivatives
  作者：Andrew G. Myers、Lydia McKinstry

  DOI：10.1021/jo952032o

  日期：1996.1.1

  Pseudoephedrine amide enolates are shown to undergo efficient alkylation reactions with epoxides as electrophiles. Reactions with monosubstituted epoxides are subject to stereochemical matching such that the pairing leading to the 1,3-syn diastereomer is a highly selective, synthetically useful process, while the pairing forming the 1,3-anti diastereomer is not. Reactions with the 1,1-disubstituted epoxide isobutylene oxide are also highly diastereoselective and synthetically useful, but ethylene oxide exhibits poor diastereoselectivity. As an alternative to the use of ethylene oxide, 2-(tert-butyldimethylsilyloxy)ethyl iodide is shown to undergo highly diastereoselective and efficient alkylation reactions with pseudoephedrine amide enolates. Interestingly, epoxides and alkyl halides are found to attack opposite pi-faces of pseudoephedrine amide enolates. The products of each of these alkylation reactions are transformed efficiently into gamma-lactones by acidic hydrolysis and into methyl ketones by the addition of methyllithium. The methodology described provides useful procedures for the synthesis of enantiomerically enriched gamma-lactones and gamma-hydroxy ketones.
• SCHMIDT, ULRICH;SIEGEL, WOLFGANG;MUNDINGER, KLAUS, TETRAHEDRON LETT., 29,(1988) N 11, 1269-1270
  作者：SCHMIDT, ULRICH、SIEGEL, WOLFGANG、MUNDINGER, KLAUS

  DOI：——

  日期：——