N-Boc-N-methylisoleucinal | 866528-89-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Boc-N-methylisoleucinal
• 英文别名: (1S,2S)-(1-formyl-2-methyl-butyl)-methyl-carbamic acid tert-butyl ester；tert-butyl N-methyl-N-[(2S,3S)-3-methyl-1-oxopentan-2-yl]carbamate
• CAS: 866528-89-4
• 化学式: C₁₂H₂₃NO₃
• 分子量: 229.32
• InChiKey: ZOKXTMUBHLTAJO-VHSXEESVSA-N

物化性质

• 沸点：
  283.0±19.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Boc-N-methylisoleucinal 在 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 1.67h， 生成 ethyl (3S,4S,5S)-3-methoxy-5-methyl-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]heptanoate
  参考文献：
  名称：

  A Synthetic Dolastatin 10 Analogue Suppresses Microtubule Dynamics, Inhibits Cell Proliferation, and Induces Apoptotic Cell Death

  摘要：

  We have synthesized eight analogues (D1-D8) of dolastatin 10 containing several unique amino acid subunits. Of these agents, D5 was found to be most effective in inhibiting both He La cell proliferation and microtubule assembly in vitro. At low nanomolar concentrations, 135 inhibited the proliferation of several types of cancer cells in culture. D5 bound to tubulin with a dissociation constant of 29.4 +/- 6 mu M. D5 depolymerized microtubules in cultured cells and produced mulitpolar spindles. At its half-maximal inhibitory concentration (15 nM), DS strongly suppressed the dynamics of individual microtubules in live MCF-7 cells. DS increased the accumulation of checkpoint proteins BubR1 and Mad2 at the kinetochoric region and caused G2/M block in these cells. The blocked cells underwent apoptosis with the activation of Jun N-terminal kinase. The results suggested that DS exerts its antiproliferative action by dampening microtubule dynamics.

  DOI：

  10.1021/jm3009629
• 作为产物：
  描述：

  叔丁氧羰基-L-异亮氨酰 N,O-二甲基羟胺 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.58h， 生成 N-Boc-N-methylisoleucinal
  参考文献：
  名称：

  Studies towards the total synthesis of Sch 56036; isoquinolinone synthesis and the synthesis of phenanthrenes

  摘要：

  The isoquinolinone hemisphere of Sch 56036 has been prepared using a modified Pomeranz-Fritsch reaction and the synthesis of the phenanthrene core has been modelled via a Suzuki coupling and subsequent ring closing metathesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.084

文献信息

• Synthesis of alpha-amino-beta-alkoxy-carboxylic acid esters
  申请人：Schmid Rudolf

  公开号：US20050272665A1

  公开（公告）日：2005-12-08

  Compounds of formula I and a process for the preparation of such compounds are disclosed.

  公开了具有I式化合物的化合物以及制备这些化合物的方法。
• Samarium Iodide-Mediated Reformatsky Reactions for the Stereoselective Preparation of β-Hydroxy-γ-amino Acids: Synthesis of Isostatine and Dolaisoleucine
  作者：Christopher G. Nelson、Terrence R. Burke

  DOI：10.1021/jo202091r

  日期：2012.1.6

  The synthesis of β-hydroxy-γ-amino acids via SmI2-mediated Reformatsky reactions of α-chloroacetyloxazolidinones with aminoaldehydes is reported. Diastereoselective coupling is demonstrated to depend on the absolute configuration of the Evans chiral auxiliary employed in the reaction, allowing erythro or threo products to be obtained selectively. The potential utility of the methodology is exemplified

  报道了通过 SmI 2介导的 α-氯乙酰恶唑烷酮与氨基醛的Reformatsky 反应合成 β-羟基-γ-氨基酸。非对映选择性偶联被证明取决于反应中使用的 Evans 手性助剂的绝对构型，允许选择性地获得赤型或苏型产物。该方法的潜在效用体现在生物相关N -Boc -isostatine ( 2b ) 和N -Boc-dolaisoleucine ( 3c )的轻松合成。
• Synthesis of α-amino-β-alkoxy-carboxylic acid esters
  申请人：Hoffmann-La Roche Inc.

  公开号：US07312343B2

  公开（公告）日：2007-12-25

  Compounds of formula I and a process for the preparation of such compounds are disclosed.

  公开了化学式I的化合物以及制备这些化合物的方法。
• US7312343B2
  申请人：——

  公开号：US7312343B2

  公开（公告）日：2007-12-25
• Studies towards the total synthesis of Sch 56036; isoquinolinone synthesis and the synthesis of phenanthrenes
  作者：Edward R. Walker、Shing Y. Leung、Anthony G.M. Barrett

  DOI：10.1016/j.tetlet.2005.07.084

  日期：2005.9

  The isoquinolinone hemisphere of Sch 56036 has been prepared using a modified Pomeranz-Fritsch reaction and the synthesis of the phenanthrene core has been modelled via a Suzuki coupling and subsequent ring closing metathesis. (c) 2005 Elsevier Ltd. All rights reserved.