tributyl(1-hydroxy-(E)-2-butenyl)stannane | 94100-69-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: tributyl(1-hydroxy-(E)-2-butenyl)stannane
• 英文别名: (E)-1-(tributylstannyl)but-2-en-1-ol；(tributyl)stannylbutenol；(E,1S)-1-tributylstannylbut-2-en-1-ol
• CAS: 94100-69-3；124752-77-8；131433-63-1
• 化学式: C₁₆H₃₄OSn
• 分子量: 361.155
• InChiKey: IJGXYMQESFFGKO-KHLYBYSVSA-N

物化性质

• 沸点：
  362.1±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tributyl(1-hydroxy-(E)-2-butenyl)stannane 以62%的产率得到
  参考文献：
  名称：

  MARSHALL, JAMES A.;GUNG, WEI YI, TETRAHEDRON LETT., 30,(1989) N7, C. 2183-2186

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-(tri-n-butylstannyl)-2-buten-1-one 在 lithium aluminium tetrahydride 、 乙醇 、 (R)-1,1'-Bi-2-naphthol 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 tributyl(1-hydroxy-(E)-2-butenyl)stannane
  参考文献：
  名称：

  Marshall, James A.; Welmaker, Gregory S.; Gung, Benjamin W., Journal of the American Chemical Society, 1991, vol. 113, # 2, p. 647 - 656

  摘要：

  DOI：

文献信息

• Regio- and Stereo-controlled Addition Reaction of Aminoallylic Stannanes to Aldehydes Mediated by Germanium Dichloride
  作者：Kensuke Suzuki、Yoshihiro Nishimoto、Hiroshi Yunoki、Kensuke Tsuruwa、Naoto Esumi、Makoto Yasuda

  DOI：10.1246/cl.180291

  日期：2018.7.5

  A GeCl2-mediated addition reaction of α-(N-phthaloylamino)allylic stannane to aldehydes was achieved to give 1,2-amino alcohol derivatives in high anti-selectivity. Various types of aromatic and aliphatic aldehydes were applicable. The synthesized N-phthaloylamino alcohols were smoothly transformed to aminoalcohols by conventional methods with no loss of stereochemistry.

  GeCl2 介导的α-(N-邻苯二甲酰氨基)烯丙基锡烷与醛的加成反应得到了具有高抗选择性的1,2-氨基醇衍生物。适用于各种类型的芳香族和脂肪族醛。合成的 N-邻苯二甲酰氨基醇通过常规方法顺利转化为氨基醇，没有立体化学损失。
• Synthesis and absolute configuration of optically active E-1-alkoxymethoxy-but-2-eny(tri-n-butyl)stannanes: stereoselective reactions with aldehydes
  作者：Vincent J. Jephcote、Andrew J. Pratt、Eric J. Thomas

  DOI：10.1039/c39840000800

  日期：——

  (1R)- and (1S)-1-[(–)-menthoxymethoxy]-E-but-2-enyl(tri-n-butyl)stannanes(5) and (6), whose configurations at C(1) were assigned by correlation with (2R)-and (2S)-pentan-2-ol, react stereoselectively on heating with benzaldeyde to give (3S,4R)- and (3R, 4R)-4hydroxy-3-methyl-cis-1,2-enol ethers (11) and (13), respectively.

  （1 R）-和（1 S）-1-[（-）-薄荷氧基甲氧基] -E -but-2-enyl（tri-n-butyl）stantanes（5）和（6），其构型在C（1 ）通过与（2 R）-和（2 S）-戊烷-2-醇的相关性分配，在加热后与苯并甲醛基立体反应，得到（3 S，4 R）-和（3 R，4 R）-4羟基3-甲基-顺式-1,2-烯醇醚（11）和（13）。
• Solid-Support Synthesis of 1,2-Diols and <i>γ</i>-Lactones Through Addition of <i>α</i>-(Benzoyloxy)crotylindium Reagents to Aldehydes
  作者：Janine Cossy、Chrystelle Rasamison、Domingo Gomez Pardo、James A. Marshall

  DOI：10.1055/s-2001-13367

  日期：——

  A procedure for the solid phase synthesis of 1,2-diols and γ-lactones from α-(hydroxy)crotylstannane has been developed through transmetalation with InBr3. A variety of 1,2-diols and γ-lactones were synthesized in satisfactory yields and, in some cases, with excellent diastereoselectivity. The products are formed free of tin contamination.

  通过 InBr3 的金属转移，开发了从 α-（羟基）巴豆基锡烷固相合成 1,2-二醇和 γ-内酯的方法。各种1,2-二醇和γ-内酯的合成都具有令人满意的产率，并且在某些情况下具有优异的非对映选择性。产品不含锡污染。
• Highly stereoselective synthesis of vicinal diols by stannous chloride-mediated addition of hydroxyallylic stannanes to aldehydes
  作者：Makoto Yasuda、Tatsuya Azuma、Kensuke Tsuruwa、Srinivasarao Arulananda Babu、Akio Baba

  DOI：10.1016/j.tetlet.2009.01.137

  日期：2009.7

  A new protocol for the synthesis of vicinal diols was accomplished by the reaction of unprotected α-hydroxymethylmetals, as hydroxymethyl anion equivalents, with aldehydes. The treatment of hydroxyallylic stannanes, which were prepared from α,β-unsaturated aldehydes and Bu3SnLi in situ, with various aldehydes gave but-3-en-1,2-diols in the presence of SnCl2. The stereochemistry of the diol and olefin

  通过未保护的α-羟甲基金属（如羟甲基阴离子当量）与醛的反应，完成了邻位二醇合成的新方案。由α，β-不饱和醛和Bu 3 SnLi原位制备的羟基锡烷与各种醛的处理在SnCl 2存在的情况下可生成3-en-1,2-二醇。二醇和烯烃部分的立体化学分别显示出顺-和E-选择性。我们提出以下反应机制；SnCl 2对羟基烯丙基锡进行金属重金属化产生重排的烯丙基锡（II）物种，该物种通过环状过渡态进行醛加成反应。未保护的羟基部分与锡（II）中心之间的严格相互作用说明了选择性。
• Chiral Transfer in the Reaction of Aminoallylic Stannanes with Carbonyls in Two Different Modes using Tin(II) and Indium(III) Halides for the Synthesis of Each Enantiomer
  作者：Makoto Yasuda、Yoshitaka Nagano、Hiroshi Yunoki、Kensuke Tsuruwa、Akio Baba

  DOI：10.1021/om500768e

  日期：2014.8.11

  The reaction of homochiral aminoallylic stannanes with aldehydes gave carbonyl adducts of amino alcohols in the presence of either SnCl2 or InBr3. Both additives afforded the products in opposite absolute stereochemical configurations. The controlled chirality was ascribed to the different transmetalation pathways of SnCl2 and InBr3.