(4R,5R)-2-phenyl-2,4,5-trimethyl-1,3-dioxolane | 141434-77-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-2-phenyl-2,4,5-trimethyl-1,3-dioxolane
• 英文别名: (4R)-2,4r,5t-trimethyl-2-phenyl-[1,3]dioxolane；(4R)-2,4r,5t-Trimethyl-2-phenyl-[1,3]dioxolan；(4R,5R)-2,4,5-trimethyl-2-phenyl-1,3-dioxolane
• CAS: 141434-77-7
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: WMAYHUYATQWWQA-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2-phenyl-2,4,5-trimethyl-1,3-dioxolane 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 反应 2.0h， 生成 4-Phenyl-1,2,4-trimethyl-3-oxa-1-pentanol
  参考文献：
  名称：

  Asymmetric synthesis at prochiral centers: substituted 1,3-dioxolanes

  摘要：

  DOI：

  10.1021/jo00338a011
• 作为产物：
  描述：

  2-(Phenylseleno)styrene 在 silica gel 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.17h， 生成 (4R,5R)-2-phenyl-2,4,5-trimethyl-1,3-dioxolane
  参考文献：
  名称：

  手性1,2-二元醇，氨基醇和二胺与乙烯基硒酮的反应合成对映体纯的1,4-二恶烷，吗啉和哌嗪

  摘要：

  容易获得的乙烯基硒酮与对映纯1,2-二醇，N-保护的1,2-氨基醇和二胺的反应分别得到了对映体纯的1,4-二恶烷，吗啉和哌嗪，收率良好至极佳。相同的程序扩展到了硫吗啉，苯并二氮杂卓和苯并x氮平的合成。通过简单，新颖地应用迈克尔引发的闭环（MIRC）反应，在碱存在的情况下，该反应在一个罐中进行。形成的杂环构成在许多药物化合物中观察到的骨架。

  DOI：

  10.1002/chem.201002593

文献信息

• Asymmetric deprotonation and complexation reactions mediated by chiral ketals as a route to ortho-disubstituted (.eta.6-arene)Cr(CO)3 complexes
  作者：Jeffrey Aube、Joseph A. Heppert、Michael L. Milligan、Mary Jane Smith、Paul Zenk

  DOI：10.1021/jo00039a012

  日期：1992.6

  A series of chiral ketals derived from an aryl ketone or aldehyde and one of several C2-symmetrical diols were converted to their corresponding (eta-6-arene)Cr(CO)s complexes. The resultant 1,3-dioxolanes were trans substituted at C-4 and C-5 by groups CH2X, where X = H (1), OCH3 (2), or N(CH3)2 (3). Ortho deprotonation was attempted on complexes 1-3 using tert-butyllithium in THF solution to afford the corresponding lithio derivatives, which were treated with a variety of electrophiles (MeOSO2F, TMSCl, Ph2C(O), Ph2PCl). Although 1 gave a complex mixture of products, complexes 2 and 3 afforded good yields of disubstituted complexes (with the exception that the lithiated derivative of 3 did not undergo methylation when treated with MeOSO2F). The stereoselectivity of the reactions was determined by NMR spectroscopy and found to be in the range of 3:1 for 2 and >9.1 for 3. The sense of diastereoselection were identified by chemical correlations (for compounds derived from 2) and by circular dichroism spectroscopy. Poor diastereoselection was obtained when this protocol was performed on the corresponding acetal ultimately derived from benzaldehyde and N,N,N',N-tetramethyl-1,4-diamino-2,3-butanediol. In addition, a related series of ortho-disubstituted arenes bearing chiral ketal or acetal substituents in the benzylic position were subjected to complexation reactions with (naphthalene)Cr(CO)3 in dibutyl ether. The best diastereoselectivity observed with this methodology was 48%, obtained with the acetal derived from o-tolualdehyde and N,N,N',N-tetramethyltartramide.
• Neish; Macdonald, Canadian Journal of Research, Section B: Chemical Sciences, 1947, vol. 25, p. 70,71, 75
  作者：Neish、Macdonald

  DOI：——

  日期：——
• RICHTER, W. J., J. ORG. CHEM., 1981, 46, N 25, 5119-5124
  作者：RICHTER, W. J.

  DOI：——

  日期：——
• Synthesis of Enantiopure 1,4-Dioxanes, Morpholines, and Piperazines from the Reaction of Chiral 1,2-Diols, Amino Alcohols, and Diamines with Vinyl Selenones
  作者：Luana Bagnoli、Catalina Scarponi、Maria Giovanna Rossi、Lorenzo Testaferri、Marcello Tiecco

  DOI：10.1002/chem.201002593

  日期：2011.1.17

  selenones with enantiopure 1,2‐diols, N‐protected‐1,2‐aminoalcohols, and diamines gave substituted enantiopure 1,4‐dioxanes, morpholines, and piperazines, respectively, in good to excellent yields. The same procedure was extended to the synthesis of thiomorpholine, benzodiazepine, and benzoxazepine. The reactions proceeded in one pot, in the presence of base, through a simple and novel application of the

  容易获得的乙烯基硒酮与对映纯1,2-二醇，N-保护的1,2-氨基醇和二胺的反应分别得到了对映体纯的1,4-二恶烷，吗啉和哌嗪，收率良好至极佳。相同的程序扩展到了硫吗啉，苯并二氮杂卓和苯并x氮平的合成。通过简单，新颖地应用迈克尔引发的闭环（MIRC）反应，在碱存在的情况下，该反应在一个罐中进行。形成的杂环构成在许多药物化合物中观察到的骨架。
• Asymmetric synthesis at prochiral centers: substituted 1,3-dioxolanes
  作者：Wolf Juergen Richter

  DOI：10.1021/jo00338a011

  日期：1981.12