3-(2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl)pent-2-enoic acid ethyl ester | 472958-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl)pent-2-enoic acid ethyl ester
• 英文别名: ethyl (E)-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pent-2-enoate
• CAS: 472958-56-8
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: XAQARRHQPGIRJR-FMIVXFBMSA-N

物化性质

• 沸点：
  391.8±37.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl)pent-2-enoic acid ethyl ester 在 4 A molecular sieve titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 L-(+)-酒石酸二乙酯 作用下， 以 乙醚 、 癸烷 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (+)-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pentane-1,3-diol
  参考文献：
  名称：

  Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans

  摘要：

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00632-4
• 作为产物：
  描述：

  2-甲氧基吡啶 在 四(三苯基膦)钯 sodium tetrahydroborate 、 甲基锂 、 二异丙胺 、 N,N-二异丙基乙胺 、 copper(l) chloride 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 22.5h， 生成 3-(2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl)pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans

  摘要：

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00632-4

文献信息

• Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins
  申请人：——

  公开号：US20030073840A1

  公开（公告）日：2003-04-17

  A method of synthesizing a compound having the formula: 1 from a compound having the formula: 2 wherein R 1 is hydrogen, fluorine, chlorine or SiR 5 R 6 R 7 , wherein R 5 , R 6 , and R 7 are independently the same or different an alkyl group or an aryl group, R 2 is an alkyl group, R 3 is a protecting group, R 4 is an alkyl group, an allyl group, a propargyl group —CO 2 H, or a benzyl group, R 8 is —CO 2 R 10 , wherein R 10 is an alkyl group or an aryl group, X 1 is OH and X 2 is H, includes the step of exposing compound (III) to at least one of an organic acid or an inorganic acid. A compound has the general formula (III).

  一种合成具有以下化学式的化合物的方法：1从具有以下化学式的化合物中进行：2其中R1为氢、氟、氯或SiR5R6R7，其中R5、R6和R7分别独立地为相同或不同的烷基基团或芳基基团，R2为烷基基团，R3为保护基团，R4为烷基基团、烯丙基团、丙炔基团、—CO2H或苄基团，R8为—CO2R10，其中R10为烷基基团或芳基基团，X1为OH，X2为H，包括将化合物(III)暴露于至少一种有机酸或无机酸中的步骤。化合物具有一般化学式(III)。
• US6723853B2
  申请人：——

  公开号：US6723853B2

  公开（公告）日：2004-04-20
• [EN] INTERMEDIATES AND METHODS OF PREPARATION OF INTERMEDIATES IN THE ENANTIOMERIC SYNTHESIS OF (20R)HOMOCAMPTOTHECINS AND THE ENANTIOMERIC SYNTHESIS OF (20R)HOMOCAMPTOTHECINS<br/>[FR] PRODUITS INTERMEDIAIRES ET PROCEDES DE PREPARATION DE PRODUITS INTERMEDIAIRES DANS LA SYNTHESE ENANTIOMERE DE (20R)HOMOCAMPTOTHECINES ET LA SYNTHESE ENANTIOMERE DE (20R)HOMOCAMPTOTHECINES
  申请人：UNIV PITTSBURGH

  公开号：WO2003018559A2

  公开（公告）日：2003-03-06

  A method of synthesizing a compound having the formula (V), from a compound having the formula (III), wherein R1 is hydrogen, fluorine, chlorine or SiR5R6R7, wherein R?5, R6, and R7¿ are independently the same or different an alkyl group or an aryl group, R2 is an alkyl group, R3 is a protecting group, R4 is an alkyl group, an allyl group, a propargyl group -CO¿2?H, or a benzyl group, R?8¿ is -CO¿2R?10, wherein R10 is an alkyl group or an aryl group, X1 is OH and X2 is H, includes the step of exposing compound (III) to at least one of an organic acid or an inorganic acid. A compound has the general formula (III).
• Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans
  作者：Ana E Gabarda、Wu Du、Thomas Isarno、Raghuram S Tangirala、Dennis P Curran

  DOI：10.1016/s0040-4020(02)00632-4

  日期：2002.8

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.