N-(2-triethylsilylpropylidene)-tert-butylamine | 102438-15-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-triethylsilylpropylidene)-tert-butylamine
• 英文别名: α-triethylsilyl t-butylimine of propionaldehyde；α-(triethylsilyl)propanal tert-butylimine；N-tert-butyl-2-triethylsilylpropan-1-imine
• CAS: 102438-15-3
• 化学式: C₁₃H₂₉NSi
• 分子量: 227.465
• InChiKey: YNHITDCCYJWRRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S)-1-[(1,1-dimethylethyl)dimethylsilyl]-4-oxo-2-azetidinecarboxaldehyde 、 N-(2-triethylsilylpropylidene)-tert-butylamine 在 偶氮二异丁腈 、 lithium 、 二苯二硫醚 作用下， 生成
  参考文献：
  名称：

  Enantioselective total synthesis of lankacidin C

  摘要：

  DOI：

  10.1021/ja00074a078
• 作为产物：
  描述：

  三乙基氯硅烷 、 N-(propylidene)-tert-butylamine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以71%的产率得到N-(2-triethylsilylpropylidene)-tert-butylamine
  参考文献：
  名称：

  A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions

  摘要：

  A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilization of five aldol reactions with a sequence of silyl nucleophiles, 7, 8, 35, 10, and 11, in the presence of stoichiometric amounts of the promoter, 1 or 2. The construction of the relative configuration between the stereogenic centers is diastereoselectively controlled by the stereochemistry of the promoter used in the enantioselective aldol reaction, which is nearly independent of that of the substrate (promoter control).

  DOI：

  10.1021/jo990342r

文献信息

• The Total Synthesis of Herbimycin A
  作者：Masaya Nakata、Tomomasa Osumi、Ari Ueno、Takenori Kimura、Tetsuro Tamai、Kuniaki Tatsuta

  DOI：10.1246/bcsj.65.2974

  日期：1992.11

  to our developed procedure, by using a regioselective epoxide opening [bis(1,2-dimethylpropyl)borane–NaBH4] and a stereoselective hydroboration (BH3·SMe2) as the key steps. This aldehyde 40 was subjected to the Brown’s diastereo- and enantioselective allylation conditions [[(Z)-3-methoxyallyl]diisopinocampheylborane] to afford the desired syn 3-methoxy-1,5-dodecadien-4-ol derivative. Subsequent three-step

  描述了除草霉素 A (1)、苯醌类安沙霉素抗生素的首次全合成。(2E,4S,5R,6S,8S)-5,6-二甲氧基-9-(4-甲氧基苄基)氧基-2,4,8-三甲基-2-壬烯醛 (40)，对应于1 的 ansa 链是由甲基 3,4-anhydro-2-deoxy-2-C-methyl-6-O-(triphenylmethyl)-α-D-altropyranoside (16) 制备的根据我们开发的程序，通过使用区域选择性环氧化物开环[双（1,2-二甲基丙基）硼烷-NaBH4]和立体选择性硼氢化反应（BH3·SMe2）作为关键步骤，制备甲基α-D-吡喃甘露糖苷。将此醛 40 进行布朗的非对映选择性和对映选择性烯丙基化条件 [[(Z)-3-甲氧基烯丙基] 二异松蒎基硼烷] 以提供所需的顺式 3-甲氧基-1,5-十二碳二烯-4-醇衍生物。
• Total Synthesis of Herbimycin A
  作者：Sophie Canova、Véronique Bellosta、Antony Bigot、Patrick Mailliet、Serge Mignani、Janine Cossy

  DOI：10.1021/ol062642i

  日期：2007.1.1

  Hsp90 has recently emerged as a promising biological target for treatment of cancer. Herbimycin A and other members of the benzoquinoid ansamycin class of natural products are known to inhibit Hsp90 activity. The total synthesis of herbimycin A was achieved from the commercially available Roche ester 1 by using allylmetals to control the stereogenic centers at C6, C7, C10, C11, and C12 and a ring-closing metathesis to control the (Z)-double bond of the (E,Z)-dienic moiety.
• Chambers, Mark S.; Thomas, Eric J., Journal of the Chemical Society. Perkin transactions I, 1997, # 4, p. 417 - 431
  作者：Chambers, Mark S.、Thomas, Eric J.

  DOI：——

  日期：——
• Toward a practical synthesis of acutiphycin. Highly stereoselective synthesis of C10-epi seco acid derivative via reaction paths shortened by using a series of chiral oxazaborolidinone-promoted aldol reactions
  作者：Mostofa Abu Hena、Chul-Sa Kim、Michio Horiike、Syun-ichi Kiyooka

  DOI：10.1016/s0040-4039(98)02553-2

  日期：1999.2
• Kang, Sung Ho; Jun, Hyuk-Sang; Youn, Joo-Hack, Synlett, 1998, # 10, p. 1045 - 1046
  作者：Kang, Sung Ho、Jun, Hyuk-Sang、Youn, Joo-Hack

  DOI：——

  日期：——