(+)-(S)-N-{2-(buta-2,3-dienyloxy)ethylidene}-2-methylpropane-2-sulfinamide | 1353342-75-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: (+)-(S)-N-{2-(buta-2,3-dienyloxy)ethylidene}-2-methylpropane-2-sulfinamide
• CAS: 1353342-75-2
• 化学式: C₁₀H₁₇NO₂S
• 分子量: 215.316
• InChiKey: ZRMOJWYBRXGXGO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 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：
  0.6
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+)-(S)-N-{2-(buta-2,3-dienyloxy)ethylidene}-2-methylpropane-2-sulfinamide 、 六甲基二锡 在 bis(η3-allyl-μ-chloropalladium(II)) 、 B-溴代邻苯二氧硼烷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以67%的产率得到(-)-(S)-2-methyl-N-[(3S,4S)-4-{1-(trimethylstannyl)vinyl}-tetrahydrofuran-3-yl]propane-2-sulfinamide
  参考文献：
  名称：

  Regulation of Diastereoselectivity in the Carbocyclization of Allenyl (S)-N-tert-Butylsulfinimines through a Three-Component Assembly

  摘要：

  Allenyl sulfinimines can be stereoselectively cyclized with hexamethylditin under palladium catalysis conditions followed by a selection of additives for an activated transmetalation. Reactivity and diastereoselectivity for the cyclization strongly depend on the characteristics of additives. A highly diastereoselective synthesis of five-membered rings is achieved from the reaction of the corresponding allenyl (5)-N-tert-butylsulfinimies through the following sequence. After the distannylation of the allenyl group with hexamethylditin catalyzed by the Pd complex, stereochemical routes are additive dependent: addition of SnCl4 affords a cis ring exclusively, whereas a trans ring is formed predominantly by the introduction of B-bromocatecholborane. Extension of the methodology to the synthesis of six-membered cis rings is achieved by using B-bromocatecholborane. Stereochemical relationships of products were unambiguously deduced by X-ray crystallography.

  DOI：

  10.1021/jo4025072
• 作为产物：
  描述：

  (2,3-butadienyloxy)acetaldehyde 、 S-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 、 二乙二醇二甲醚 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到(+)-(S)-N-{2-(buta-2,3-dienyloxy)ethylidene}-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Regulation of Diastereoselectivity in the Carbocyclization of Allenyl (S)-N-tert-Butylsulfinimines through a Three-Component Assembly

  摘要：

  Allenyl sulfinimines can be stereoselectively cyclized with hexamethylditin under palladium catalysis conditions followed by a selection of additives for an activated transmetalation. Reactivity and diastereoselectivity for the cyclization strongly depend on the characteristics of additives. A highly diastereoselective synthesis of five-membered rings is achieved from the reaction of the corresponding allenyl (5)-N-tert-butylsulfinimies through the following sequence. After the distannylation of the allenyl group with hexamethylditin catalyzed by the Pd complex, stereochemical routes are additive dependent: addition of SnCl4 affords a cis ring exclusively, whereas a trans ring is formed predominantly by the introduction of B-bromocatecholborane. Extension of the methodology to the synthesis of six-membered cis rings is achieved by using B-bromocatecholborane. Stereochemical relationships of products were unambiguously deduced by X-ray crystallography.

  DOI：

  10.1021/jo4025072