α-<(tert-Butyldimethylsilyl)oxy>-α-(3,4-dimethoxyphenyl)acetonitrile | 131701-93-4

• 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: α-<(tert-Butyldimethylsilyl)oxy>-α-(3,4-dimethoxyphenyl)acetonitrile
• 英文别名: α-(t-butyldimethylsilyloxy)-α-(3,4-dimethoxyphenyl)acetonitrile；2-[Tert-butyl(dimethyl)silyl]oxy-2-(3,4-dimethoxyphenyl)acetonitrile
• CAS: 131701-93-4
• 化学式: C₁₆H₂₅NO₃Si
• 分子量: 307.465
• InChiKey: ISADDOHXXODAQG-UHFFFAOYSA-N

物化性质

• 沸点：
  364.4±42.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-<(tert-Butyldimethylsilyl)oxy>-α-(3,4-dimethoxyphenyl)acetonitrile 在 palladium on activated charcoal MoO5*pyridine*HMPA 、 potassium hexamethyldisilazane 、 二乙基异丙基胺 、 硫酸 、 四丁基氟化铵 、 氢气 、 L-Selectride 、 sodium hydride 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 epitrachelogenin
  参考文献：
  名称：

  α-取代的顺式-α，β-二苄基-γ-丁内酯的高度立体选择性合成

  摘要：

  α-替补顺-α，β二苄基γ丁内酯（1）中以良好的收率合成以高度非对映方式经由亲电加成反应到β，γ二取代的α苄基γ丁内酯的烯醇化物的金属（2）作为关键步骤。

  DOI：

  10.1016/s0040-4039(00)73562-3
• 作为产物：
  描述：

  氰化钾 、 3,4-二甲氧基苯甲醛 、 叔丁基二甲基氯硅烷 在 zinc(II) iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以88%的产率得到α-<(tert-Butyldimethylsilyl)oxy>-α-(3,4-dimethoxyphenyl)acetonitrile
  参考文献：
  名称：

  Efficient Syntheses of 1-Arylnaphthalene Lignan Lactones and Related Compounds from Cyanohydrins

  摘要：

  1-Arylnaphthalene lignan lactones were synthesized in good yields from O-(tert-butyldimethylsilyl)cyanohydrins in two steps based on a conjugate addition-aldol reaction, followed by acid-catalyzed closure to form the naphthalene ring. 4-Hydroxy-1-arylnaphthalene lignan lactones were also synthesized by conjugate addition-aldol reaction, followed by aromatization-lactonization.

  DOI：

  10.1021/jo00119a041

文献信息

• A new two-step synthesis of 1-arylnaphthalene lignans from cyanohydrins
  作者：Tsuyoshi Ogiku、Masahiko Seki、Masami Takahashi、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1016/s0040-4039(00)97879-1

  日期：1990.1

  1-Arylnaphthalene lignans were synthesized in good yields from O-t-butyldimethylsilylcyanohydrins in two steps based on a new approach involving a tandem conjugate addition-aldol reaction, followed by an acid-catalyzed construction of the naphthalene ring.

  基于涉及串联共轭加成-醛醇缩合反应的新方法，然后通过酸催化的萘环的构建，由O-叔丁基二甲基甲硅烷基氰醇分两步以高收率合成了1-芳基萘木酚素。
• Syntheses of Aryltetralin Lignans: Concise Syntheses of (±)-Isopodophyllotoxone, (±)-Picropodophyllone and Their Related Compounds
  作者：Tsuyoshi Ogiku、Shin-ichi Yoshida、Tooru Kuroda、Masami Takahashi、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1246/bcsj.65.3495

  日期：1992.12

  (±)-Isopodophyllotoxone and (±)-picropodophyllone were synthesized stereoselectively from the O-(t-butyldimethylsilyl) cyanohydrins (3a) in good yields. This new method was successfully applied to the syntheses of a variety of lignans of the aryltetralin series.

  (±)-异鬼臼酮和 (±)-鬼臼苦素是由 O-(叔丁基二甲基甲硅烷基) 氰醇 (3a) 立体选择性合成的，收率良好。这种新方法已成功应用于芳基四氢萘系列多种木脂素的合成。
• Stereoselective Syntheses of <i>Cis</i>- and <i>Trans</i>-Isomers of α-Hydroxy-α,β-dibenzyl-γ-butyrolactone Lignans:  New Syntheses of (±)-Trachelogenin and (±)-Guayadequiol
  作者：Yasunori Moritani、Chiaki Fukushima、Tatsuzo Ukita、Toshikazu Miyagishima、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1021/jo9601932

  日期：1996.1.1

  Cis- and trans-isomers of alpha-hydroxy-alpha,beta-dibenzyI-gamma-butyrolactone lignans 1a,d-g and 2a,c,d were stereoselectively synthesized in good yields based on the electrophilic addition to the metal enolate of alpha-benzyl-gamma-butyolactone derivatives 1l-o and 3 as a key step, This method was applied to the syntheses of (+/-)-trachelogenin and (+/-)-guayadequiol, representative examples of the trans- and cis-isomers of alpha-hydroxy-alpha,beta-dibenzyl-y-butyrolactone lignan series.
• Moritani, Yasunori; Ukita, Tatsuzo; Hiramatsu, Hajime, Journal of the Chemical Society. Perkin transactions I, 1996, # 22, p. 2747 - 2754
  作者：Moritani, Yasunori、Ukita, Tatsuzo、Hiramatsu, Hajime、Okamura, Kimio、Ohmizu, Hiroshi、Iwasaki, Tameo

  DOI：——

  日期：——
• Enzyme-catalyzed Dediastereomerization of Dibenzylbutanolides by Plant Cell Cultures
  作者：Masumi Takemoto、Yuki Matsuoka、Kiyoshi Tanaka、Kazuo Achiwa、Nikolay Stoynov、James Peter Kutney

  DOI：10.3987/com-01-s(k)22

  日期：——

  We have been developed a novel biocatalytic dediastereornerization method, i. e., reactions allowing the transformation of two diastereorners into one diastereomer in quantitative yield. When a mixture of two diastereomers (4R*-5) and (4S*-5) (1:1 ratio) was subjected to Catharanthus roseus cells in B5 medium, dediastereornerization took place to give a single diastereomer (4R*-5) in 80 % chemical yield with 100 % diastereomeric excess and 0 % enantiomeric excess.