(R)-4-<(tert-butyldimethylsilyl)oxy>-1-bromopentane | 132260-58-3

• 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: (R)-4-<(tert-butyldimethylsilyl)oxy>-1-bromopentane
• 英文别名: (R)-(5-bromopentan-2-yloxy)(tert-butyl)dimethylsilane；[(2R)-5-bromopentan-2-yl]oxy-tert-butyl-dimethylsilane
• CAS: 132260-58-3
• 化学式: C₁₁H₂₅BrOSi
• 分子量: 281.308
• InChiKey: WWWCUAMWXAAUCX-SNVBAGLBSA-N

物化性质

• 沸点：
  68-70 °C(Press: 0.55 Torr)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-4-<(tert-butyldimethylsilyl)oxy>-1-bromopentane 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 216.0h， 生成 玉米烯酮
  参考文献：
  名称：

  Synthesis of .beta.-resorcylic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-zearalenone

  摘要：

  The beta-resorcylic macrolides are a class of naturally occurring 12- and 14-membered macrolides. Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest. In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct beta-resorcylic macrolides. The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones. This methodology was then used to prepare (S)-zearalenone (1).

  DOI：

  10.1021/jo00008a053
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 四溴化碳 、 双氧水 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 47.0h， 生成 (R)-4-<(tert-butyldimethylsilyl)oxy>-1-bromopentane
  参考文献：
  名称：

  Synthesis of .beta.-resorcylic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-zearalenone

  摘要：

  The beta-resorcylic macrolides are a class of naturally occurring 12- and 14-membered macrolides. Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest. In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct beta-resorcylic macrolides. The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones. This methodology was then used to prepare (S)-zearalenone (1).

  DOI：

  10.1021/jo00008a053

文献信息

• Synthesis of (+)-xestodecalactone A
  作者：G. Nagendra Reddy、Gudisela Mura Reddy、Gattu Sridhar、K. R. S Prasad

  DOI：10.1080/14786419.2021.1941948

  日期：2022.11.2

  Abstract The total synthesis of Benzannulated macrolide, (+)-Xestodecalactone A was accomplished starting from commercially available enantiomerically pure propylene oxide and 3,5-dihydroxyphenylacetic acid using Grignard reaction, alkylation of 1,3-dithiane and Yamaguchi macrolactonisation as key steps.

  摘要 苯环化大环内酯、(+)-Xestodecalactone A 的全合成是从市售的对映体纯环氧丙烷和 3,5-二羟基苯乙酸开始，使用格氏反应、1,3-二噻烷的烷基化和 Yamaguchi 大环内酯化作为关键步骤完成的。
• Total synthesis of diplodialides C and D
  作者：Vyasabhattar Ramanujan、Chebolu Naga Sesha Sai Pavan Kumar

  DOI：10.24820/ark.5550190.p010.703

  日期：——

  A highly convergent, stereoselective total synthesis of diplodialides C and D is described. The protocol involves the use of regioselective ring opening of a chiral epoxide, sequential double alkylation of 1,3-dithiane with a bromide and a chiral epoxide, hydroboration and Yamaguchi macrolactonisation as key steps.

  描述了二倍二内酯 C 和 D 的高度收敛、立体选择性全合成。该协议涉及使用手性环氧化物的区域选择性开环、1,3-二噻烷与溴化物和手性环氧化物的顺序双烷基化、硼氢化和 Yamaguchi macrolactonisation 作为关键步骤。
• KALIVRETENOS, A.;STILLE, J. K.;HEGEDUS, L. S., J. ORG. CHEM., 56,(1991) N, C. 2883-2894
  作者：KALIVRETENOS, A.、STILLE, J. K.、HEGEDUS, L. S.

  DOI：——

  日期：——