tert-butyl 2-[(S)-[(4-methylphenyl)sulfonyl-prop-2-ynylamino]-phenylmethyl]prop-2-enoate | 1383438-04-7

• 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)sulfonyl-prop-2-ynylamino]-phenylmethyl]prop-2-enoate
• CAS: 1383438-04-7
• 化学式: C₂₄H₂₇NO₄S
• 分子量: 425.549
• InChiKey: UVXHKOZVHNCYHR-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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)sulfonyl-prop-2-ynylamino]-phenylmethyl]prop-2-enoate 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 4-甲基-N-(丙-2-炔-1-基)苯-1-磺酰胺
  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

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 reaction of aza-1,6-enyne compounds using allyltributyltin
  作者：Akio Kamimura、Koichiro Miyazaki、Takuji Kawamoto、Hidemitsu Uno

  DOI：10.1016/j.tet.2016.04.078

  日期：2016.12

  The radical cascade reaction of allyltin with aza-1,6-enyne compounds was studied. Optically active aza-1,6-enynes underwent a radical cascade process in the presence of a high concentration of allyltributyltin to give stannolanes as the major isomer. Piperidines were also observed in small amounts when an allylic unit was introduced stereoselectively to the trans-position of the aryl group at the

  研究了烯丙基锡与aza-1,6-enyne化合物的自由基级联反应。在高浓度的烯丙基三丁基锡的存在下，光学活性的aza-1,6-enynes经历了自由基级联过程，从而得到锡诺烷作为主要异构体。当将烯丙基单元立体选择性地引入C 2位置的芳基的转位时，也观察到少量的哌啶。随着锡试剂的浓度，产物的产率急剧下降。哌啶中环戊亚甲基上的E / Z选择性取决于反应温度，并且在30℃下进行反应时几乎增加一倍。在这项研究中，讨论了自由基级联反应的机理。
• 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.