O-(1-tert-butyl-2,3-butadienyl) N-tosylcarbamate | 131141-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-(1-tert-butyl-2,3-butadienyl) N-tosylcarbamate
• 英文别名: 1-t-butyl-2,3-butadienyl tosylcarbamate
• CAS: 131141-50-9
• 化学式: C₁₆H₂₁NO₄S
• 分子量: 323.413
• InChiKey: XXNNCXXKJLQVAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  O-(1-tert-butyl-2,3-butadienyl) N-tosylcarbamate 在 silver cyanate 、 三乙胺 作用下， 以 苯 为溶剂， 反应 17.0h， 生成 trans-N-p-toluenesulfonyl-5-t-butyl-4-vinyl-2-oxazolidinone
  参考文献：
  名称：

  Silver(I)-Catalyzed Aminocyclization of 2,3-Butadienyl and 3,4-Pentadienyl Carbamates: An Efficient and Stereoselective Synthesis of 4-Vinyl-2-oxazolidinones and 4-Vinyltetrahydro-2H-1,3-oxazin-2-ones

  摘要：

  银(I)盐与适当的碱（主要是三乙胺）催化N-取代的2,3-丁二烯基氨基甲酸酯1（苯，50°C）进行环化反应，以良好产率得到4-乙烯基-2-恶唑啉酮2。立体选择性（反式2/顺式2）从C5-甲基的1.4到C5-苯基、异丙烯基和叔丁基衍生物的>30不等。3,4-戊二烯基对甲苯磺酰氨基甲酸酯3，作为1的碳数多一的同系物，经历了类似的环化反应，以合成上有用的产率得到4-乙烯基四氢-2H-1,3-恶嗪-2-酮4，并且其反式选择性高于1。

  DOI：

  10.1246/bcsj.68.1689
• 作为产物：
  描述：

  特戊醛 生成 O-(1-tert-butyl-2,3-butadienyl) N-tosylcarbamate
  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

• Silver(I) catalyzed amino cyclization of O-(2,3-butadienyl) carbamates: an efficient and stereoselective synthesis of 4-vinyl-2-oxazolidinones
  作者：Masanari Kimura、Keigo Fugami、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1016/0040-4039(91)80169-7

  日期：1991.10

  Silver(I) salts catalyze an amino cyclization of O-(2,3-butadienyl) N-tosyl-carbamates to provide mixtures of cis and trans-5-substituted N-tosyl-4-vinyl-2-oxazolidinones, the trans-isomers predominantly or exclusively.

  银（I）盐催化O-（2,3-丁二烯基）N-甲苯磺酰基氨基甲酸酯的氨基环化反应，提供顺式和反式-5-取代的N-甲苯磺酰基-4-乙烯基-2-恶唑烷酮的混合物，反式-异构体占主导地位或排他性。
• Palladium-catalyzed regio- and stereoselective allylamination of allenic alcohols
  作者：Masanari Kimura、Keigo Fugami、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1021/jo00050a001

  日期：1992.11

  Palladium [PdCl2(PhCN)2 or Pd2(dba)3.CHCl3] catalyzes the reaction of O-(2,3-butadienyl) N-tosylcarbamates 1 with allylic chlorides to selectively provide trans-4,5-disubstituted oxazolidin-2-ones 2 in good yields. Under similar conditions, Pd(PPh3)4 catalyzes an N-allylation of 1 to give 3, and chloro-pi-allylpalladium(II) dimer promotes a dimerization of 1g and gives 4 as a major product together with 2.
• Palladium-Catalyzed Stereoselective Allylaminocyclization and 1,3-Butadien-2-ylaminocyclization of Allenyl Tosylcarbamates
  作者：Masanari Kimura、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1021/jo00117a031

  日期：1995.6

  Palladium [PdCl2(PhCN)(2) or Pd-2(dba)(3) . CHCl3 (dba = dibenzylideneacetone)], in the presence of a base (Et(3)N or K2CO3) in THF at room temperature, catalyzes an allylaminocyclization of 2,3-butadienyl tosylcarbamates 1 with allylic chlorides to selectively provide trans-4,5-disubstituted 2-oxazolidinones 2 in good yields. Under similar conditions, Pd(PPh(3))(4) catalyzes an N-allylation of 1 to give 3. A limited number of 3,4-pentadienyl tosylcarbamates 5 undergo the allylaminocyclization to provide tetrahydro-1,3-oxazin-2-ones 6. In the absence of an allylic chloride, Pd(PPh(3))(4) and PdCl2(PhCN)(2) catalyze a formal dimerization of 1 to provide C-4-triene-substituted 2-oxazolidinones 4 in moderate to good yields.
• 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.
• Pd2+-catalyzed oxidative aminocarbonylation of O-2,3-butadienyl and O-3,4-pentadienyl N-tosylcarbamates
  作者：Masanari Kimura、Naoto Saeki、Shigeru Uchida、Hiroto Harayama、Shuji Tanaka、Keigo Fugami、Yoshinao Tamaru

  DOI：10.1016/s0040-4039(00)60413-6

  日期：1993.11

  Pd2+-catalyzed aminocarbonylation of O-2,3-butadienyl 1 and O-3,4-pentadienyl carbamates 5 stereoselectively provides 4-(1-methoxycarbonylvinyl)-1,3-oxazolidin-2-ones 2 and 4-(1-methyoxycarbonylvinyl)-1,3-oxazin-2-ones 6, respectively, in high yields.