(R)-tert-butyl(hept-6-en-2-yloxy)diphenylsilane | 929554-08-5

• 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)-tert-butyl(hept-6-en-2-yloxy)diphenylsilane
• 英文别名: tert-butyl-[(2R)-hept-6-en-2-yl]oxy-diphenylsilane
• CAS: 929554-08-5
• 化学式: C₂₃H₃₂OSi
• 分子量: 352.592
• InChiKey: ISHXIBGRKYPHLN-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  (R)-tert-butyl(hept-6-en-2-yloxy)diphenylsilane 在 Grubbs catalyst first generation 吡啶 、 2,4,6-三氯苯甲酰氯 、 氢氟酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 91.0h， 生成 diplodialide B
  参考文献：
  名称：

  Stereoselective synthesis of (+)-diplodialides-B, C and a formal synthesis of (+)-diplodialide-A by ring-closing metathesis approach

  摘要：

  Stereoselective synthesis of diplodialides-B and C and the formal synthesis of diplodialide-A are reported. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centers, while a ring-closing metathesis strategy was used for the construction of the lactone ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.045
• 作为产物：
  描述：

  (5R)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxyhexan-1-ol 在 正丁基锂 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 8.5h， 生成 (R)-tert-butyl(hept-6-en-2-yloxy)diphenylsilane
  参考文献：
  名称：

  Stereoselective synthesis of (+)-diplodialides-B, C and a formal synthesis of (+)-diplodialide-A by ring-closing metathesis approach

  摘要：

  Stereoselective synthesis of diplodialides-B and C and the formal synthesis of diplodialide-A are reported. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centers, while a ring-closing metathesis strategy was used for the construction of the lactone ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.045

文献信息

• Total synthesis and stereochemical revision of relgro and 10′-oxorelgro
  作者：Janardhan Gaddam、G. Sudhakar Reddy、Kanakaraju Marumudi、Ajit C. Kunwar、Jhillu S. Yadav、Debendra K. Mohapatra

  DOI：10.1039/c9ob00838a

  日期：——

  The first asymmetric total synthesis and stereochemical assignments of 10-membered macrolactones relgro and 10'-oxorelgro are disclosed. To this end, palladium-catalyzed Stille coupling, the Mitsunobu reaction, ring-closing metathesis, EDCI promoted coupling and the Jacobsen hydrolytic kinetic resolution are used as key steps. The total synthesis followed by thorough evaluation of the optical rotation

  公开了10元大内酯relgro和10'-氧杂睾酮的第一不对称全合成和立体化学分配。为此，关键步骤是使用钯催化的Stille偶联，Mitsunobu反应，闭环复分解，EDCI促进的偶联以及Jacobsen水解动力学拆分。总合成之后，对旋光度和CD光谱数据进行了全面评估，从而改变了relgro和10'-oxorelgro的C-6'绝对构型。此外，relgro首次报道了1H和13C NMR数据。
• Asymmetric Total Synthesis of (2E)-Macrolactin 3
  作者：Debendra K. Mohapatra、Aedula Vishnu V. Reddy、Utkal Mani Choudhury、Akella V. S. Sarma

  DOI：10.1055/a-1957-3966

  日期：2023.1

  Asymmetric total synthesis of (2E)-macrolactin 3 has been accomplished in a highly convergent manner utilizing our earlier developed tandem isomerization followed by C–O and C–C bond-forming reaction, Sharpless asymmetric dihydroxylation, and a late-stage intramolecular Heck coupling reaction. Comparison of the NMR spectra of the coupled product and thorough analysis of the 2D NMR data of the final

  (2 E )-macrolactin 3 的不对称全合成已经以高度收敛的方式完成，利用我们早期开发的串联异构化，然后是 C-O 和 C-C 键形成反应、Sharpless 不对称二羟基化和后期分子内 Heck偶联反应。比较偶联产物的 NMR 光谱和对最终化合物的 2D NMR 数据的全面分析得出结论，即 C2 上的Z双键在偶联反应过程中发生了异构化。
• Enantioselective synthesis of (2R,13R,8Z)-2,13-diacetoxy-8-heptadecene, the major component of the sex pheromone of the pear leaf midge, Dasineura pyri
  作者：Yun Zhou、Pengfei Yang、Shuoning Li、Lifeng Wang、Jingwei Yin、Jiangchun Zhong、Yanhong Dong、Shangzhong Liu、Min Wang、Qinghua Bian

  DOI：10.1016/j.tetasy.2017.01.010

  日期：2017.2

  The first enantioselective synthesis of (2R,13R,8Z)-2,13-diacetoxy-8-heptadecene 1, the major component of the sex pheromone of the pear leaf midge, Dasineura pyri, has been achieved. The key steps include the (R,R)-BINOL/Ti(OiPr)(4) catalyzed alkynylzinc addition to an unsaturated aldehyde, the ring opening of the chiral epoxide with a Grignard reagent, and the partial reduction of an acetylenic diol ester to a (Z)-olefinic diol ester with hydrogen and P2-Ni. (C) 2017 Elsevier Ltd. All rights reserved.
• A chemoenzymatic asymmetric synthesis of methyl (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate, a component of Mycosphaerella rubella
  作者：Anubha Sharma、Sunita Gamre、Subrata Chattopadhyay

  DOI：10.1016/j.tetasy.2009.04.004

  日期：2009.6

  The first asymmetric synthesis of (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate has been developed. The key steps of the synthesis were the use of an efficient lipase-catalyzed acylation, a chiral template-driven enantiocontrolled allylation for introducing the stereogenic centers, and a cross-meta thesis for controlling the C-8 olefin geometry. (C) 2009 Elsevier Ltd. All rights reserved.