| 131141-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 131141-46-3
• 化学式: C₁₈H₂₃NO₄S
• 分子量: 349.451
• InChiKey: AZHLTTMKQFWXSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  在 碘 作用下， 生成
  参考文献：
  名称：

  A highly stereoselective conversion of α-allenic alcohols to syn-1,2-diol derivatives

  摘要：

  Alpha-Allenic alcohols 4 are converted with high diastereoselectivity via an iodocyclization process into the syn-1,2-diol derivatives 10.

  DOI：

  10.1016/s0040-4039(00)91949-x
• 作为产物：
  描述：

  环己烷基甲醛 生成
  参考文献：
  名称：

  A highly stereoselective conversion of α-allenic alcohols to 1,2-syn amino alcohol derivatives via iodocarbamation

  摘要：

  DOI：

  10.1016/s0040-4039(00)97592-0

文献信息

• Iodocyclization of the (tolylsulfonyl)- and (trichloroacetyl)carbamates of secondary .alpha.-allenic alcohols. Highly diastereoselective synthesis of syn-1,2-amino alcohols and trans-5-alkyl-1-oxo-2-oxazolidine-4-carboxylic acids
  作者：Richard W. Friesen、Aleksandra E. Kolaczewska

  DOI：10.1021/jo00016a016

  日期：1991.8

  The iodocyclization of tosyl- and (trichloroacetyl)carbamates 9 and 10, respectively, of secondary alpha-allenic alcohols is described. The cyclofunctionalization reactions are highly diastereoselective, providing trans-5-alkyl-4-(1-iodoethylene)-2-oxazolidinones 11 and 12 as the major diastereomers in ratios of 6.3:1 to > 99: < 1. The mechanism of cyclization involves the initial formation of diiodides resulting from the addition of I2 to the terminal olefin of the allene moiety, followed by a kinetically controlled intramolecular SN2' displacement of iodide. Hydrolysis and acetylation of the N-tosyloxazolidinones 11 provide syn-1,2-amino alcohol derivatives 15. Alternatively, ozonolysis of the vinyl iodides derived from the cyclization of the (trichloroacetyl)carbamates 12 provides a novel, efficient, and highly diastereoselective route to trans-5-alkyl-2-oxazolidinone-4-carboxylic acids 25 and esters 26.
• Palladium(0)-catalyzed coupling of allenyl N-tosylcarbamates with hypervalent iodonium salts
  作者：Suk-Ku Kang、Tae-Gon Baik、Yun Hur

  DOI：10.1016/s0040-4020(99)00340-3

  日期：1999.5

  The palladium Pd(PPh3)(4)-catalyzed coupling reaction of allenyl N-tosylcarbamates with hypervalent iodonium salts afforded the cyclized trans-5-substituted oxazolidinones, 3-oxazin-2-ones, and higher membered carbamates under mild conditions, (C) 1999 Elsevier Science Ltd. All rights reserved.
• FRIESEN, RICHARD W., TETRAHEDRON LETT., 31,(1990) N0, C. 4249-4250
  作者：FRIESEN, RICHARD W.

  DOI：——

  日期：——
• A highly stereoselective conversion of α-allenic alcohols to syn-1,2-diol derivatives
  作者：Richard W. Friesen、André Giroux

  DOI：10.1016/s0040-4039(00)91949-x

  日期：1993.3

  Alpha-Allenic alcohols 4 are converted with high diastereoselectivity via an iodocyclization process into the syn-1,2-diol derivatives 10.
• A highly stereoselective conversion of α-allenic alcohols to 1,2-syn amino alcohol derivatives via iodocarbamation
  作者：Richard W Friesen

  DOI：10.1016/s0040-4039(00)97592-0

  日期：1990.1