tert-butyl 2-[(S)-(4-methylphenyl)-[(4-methylphenyl)sulfonyl-prop-2-ynylamino]methyl]prop-2-enoate | 1227307-69-8

• 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: tert-butyl 2-[(S)-(4-methylphenyl)-[(4-methylphenyl)sulfonyl-prop-2-ynylamino]methyl]prop-2-enoate
• CAS: 1227307-69-8
• 化学式: C₂₅H₂₉NO₄S
• 分子量: 439.576
• InChiKey: JVTPNIJZPLMRQL-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[(S)-(4-methylphenyl)-[(4-methylphenyl)sulfonyl-prop-2-ynylamino]methyl]prop-2-enoate 在 Au(PPh₃)Cl 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以57%的产率得到(S)-2,6-dimethylene-5-(p-tolyl)-4-tosyl-1,4-oxazepan-7-one
  参考文献：
  名称：

  Gold(I)-Catalyzed Synthesis of Optically Active 1,4-Oxazepan-7-ones

  摘要：

  Optically active seven-membered lactones, dimethyleneoxazepanones, were readily prepared in good yields from chiral beta-(N-propargylic)-amino-alpha-methylene carboxylic add tert-butyl esters in the presence of catalytic amounts of Ph3PAuCl and Cu(OTf)(2) A smooth 7-exo-dig cyclization was observed.

  DOI：

  10.1021/jo501254x
• 作为产物：
  描述：

  (S)-tert-butyl 2-((4-methylphenylsulfonamido)(p-tolyl)methyl)acrylate 、 3-溴丙炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到tert-butyl 2-[(S)-(4-methylphenyl)-[(4-methylphenyl)sulfonyl-prop-2-ynylamino]methyl]prop-2-enoate
  参考文献：
  名称：

  光学活性氮杂-Baylis-Hillman加合物的分子内Pauson-Khand反应

  摘要：

  通过光学活性的亚磺胺的硫代-迈克尔/亚氨基-羟醛多米诺反应制备的氮杂-Baylis-Hillman加合物的分子内Pauson-Khand反应进行了检测，并得到了具有光学活性的顺式和反式-吡咯烷稠合的环戊烯酮立体选择性的方式。

  DOI：

  10.1016/j.tetlet.2010.02.115

文献信息

• Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction
  作者：Koichiro Miyazaki、Yu Yamane、Ryuichiro Yo、Hidemitsu Uno、Akio Kamimura

  DOI：10.3762/bjoc.9.149

  日期：——

  Bicyclodihydrosiloles were readily prepared from optically active enyne compounds by a radical cascade reaction triggered by tris(trimethylsilyl)silane ((Me3Si)3SiH). The reaction was initiated by the addition of a silyl radical to an alpha,beta-unsaturated ester, forming an alpha-carbonyl radical that underwent radical cyclization to a terminal alkyne unit. The resulting vinyl radical attacked the silicon atom in an

  通过由三（三甲基甲硅烷基）硅烷（（Me3Si）3SiH）引发的自由基级联反应，可以很容易地从光学活性烯炔化合物制备双环二氢硅醇。该反应通过将甲硅烷基加入 α,β-不饱和酯引发，形成 α-羰基自由基，该自由基环化成末端炔单元。所得乙烯基自由基以 SHi 方式攻击硅原子，得到二氢硅酮。该反应优先形成双环硅氧烷的反式异构体，选择性约为 7:3 至 9:1。
• A Radical Cascade Cyclization To Prepare Dihydrothiophenes Induced by Thiyl Radicals as Sulfur Biradical Equivalents
  作者：Akio Kamimura、Koichiro Miyazaki、Yu Yamane、Ryuichiro Yo、Shingo Ishikawa、Hidemitsu Uno、Michinori Sumimoto

  DOI：10.1021/jo400975t

  日期：2013.8.16

  Bicyclic dihydrothiophenes are readily prepared by a radical cascade cyclization reaction triggered by the addition of a thiyl radical under thermal or photoirradiation conditions. The translocated radical attacks the sulfur atom in the initial radical donor unit in an S(H)i manner. Sufficient stereoselectivity is achieved when a large excess of disulfide is used for the reaction under photoirradiation conditions. The reaction in the absence of solvents provides vinylsulfides instead of dihydrothiophenes. Thus, the sulfur atom in the thiyl radical serves as a sulfur biradical synthetic equivalent.
• Gold(I)-Catalyzed Synthesis of Optically Active 1,4-Oxazepan-7-ones
  作者：Akio Kamimura、Yu Yamane、Ryuichiro Yo、Toshiyuki Tanaka、Hidemitsu Uno

  DOI：10.1021/jo501254x

  日期：2014.8.15

  Optically active seven-membered lactones, dimethyleneoxazepanones, were readily prepared in good yields from chiral beta-(N-propargylic)-amino-alpha-methylene carboxylic add tert-butyl esters in the presence of catalytic amounts of Ph3PAuCl and Cu(OTf)(2) A smooth 7-exo-dig cyclization was observed.
• Intramolecular Pauson–Khand reaction of optically active aza-Baylis–Hillman adducts
  作者：Shingo Ishikawa、Fumiaki Noguchi、Hidemitsu Uno、Akio Kamimura

  DOI：10.1016/j.tetlet.2010.02.115

  日期：2010.4

  The intramolecular Pauson–Khand reaction of aza-Baylis–Hillman adducts, which were prepared through the thio-Michael/imino-aldol domino reaction of optically active sulfinimines, was examined and gave optically active cis- and trans-pyrrolidine-fused cyclopentenones in a stereoselective manner.

  通过光学活性的亚磺胺的硫代-迈克尔/亚氨基-羟醛多米诺反应制备的氮杂-Baylis-Hillman加合物的分子内Pauson-Khand反应进行了检测，并得到了具有光学活性的顺式和反式-吡咯烷稠合的环戊烯酮立体选择性的方式。