(-)-(1R,2S)-1,2-dihydro-1-(3,4,5-trimethoxyphenyl)-2-(hydroxymethyl)-3-formylnaphthalene | 171296-56-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: (-)-(1R,2S)-1,2-dihydro-1-(3,4,5-trimethoxyphenyl)-2-(hydroxymethyl)-3-formylnaphthalene
• 英文别名: (7S,8R)-7-(hydroxymethyl)-8-(3,4,5-trimethoxyphenyl)-7,8-dihydrobenzo[f][1,3]benzodioxole-6-carbaldehyde
• CAS: 171296-56-3
• 化学式: C₂₂H₂₂O₇
• 分子量: 398.412
• InChiKey: INPRFVJKDWYGGM-IIBYNOLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-(1R,2S)-1,2-dihydro-1-(3,4,5-trimethoxyphenyl)-2-(hydroxymethyl)-3-formylnaphthalene 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 5.0h， 以25%的产率得到(5R,5aS)-5-(3,4,5-trimethoxyphenyl)-5a,6-dihydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
  参考文献：
  名称：

  C-9氧化鬼臼毒素衍生物的合成和细胞毒性评估。

  摘要：

  已经制备了一系列缺乏内酯环并且在C-9位被氧化的鬼臼毒素和鬼臼醛衍生物。C-9处考虑的官能团是羧酸和几种衍生物，例如酯，酰胺，腈或酸酐。合成的化合物在微摩尔水平上具有细胞毒性，尽管其效力和选择性均低于母体化合物，从而揭示了C-9亲电特性对这些环木脂素的效力和选择性的影响。

  DOI：

  10.1016/j.bmc.2006.12.008
• 作为产物：
  描述：

  鬼臼毒素 在 氢氧化钾 、 lithium aluminium tetrahydride 、 三甲基氯硅烷 、 草酰氯 、 三氟化硼乙醚 、 二甲基亚砜 、 三乙胺 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 28.0h， 生成 (-)-(1R,2S)-1,2-dihydro-1-(3,4,5-trimethoxyphenyl)-2-(hydroxymethyl)-3-formylnaphthalene
  参考文献：
  名称：

  Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring

  摘要：

  Several cyclolignans lacking of the lactone moiety can easily be prepared from naturally occurring lignans such as podophyllotoxin and deoxypodophyllotoxin by simple chemical transformations. Their cytotoxicity has been studied in four tumoral cell lines. Most of the compounds show similar effects in all the neoplastic systems tested, except the aldehyde 9 (methyl 9-deoxy-9-oxo-alpha-apopicropodophyllate) and the hydrazones 16 and 17 which show a highly selective cytotoxicity towards HT-29 human colon carcinoma. Additionally, several molecular modeling studies have been done with aldehyde 9 and the corresponding saturated aldehyde 13 in comparison with podophyllotoxin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10042-4

文献信息

• Synthesis and antineoplastic activity of cyclolignan aldehydes
  作者：Marina Gordaliza、M Angeles Castro、José M Miguel del Corral、M Luisa López-Vázquez、Pablo A. García、M Dolores García-Grávalos、Arturo San Feliciano

  DOI：10.1016/s0223-5234(00)00176-8

  日期：2000.8

  Several aldehydes related to methyl 9-deoxy-9-oxo-alpha-apopicropodophyllate, a selective antitumour agent against the HT-29 colon carcinoma, have been prepared and evaluated for their cytotoxic activities on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28). All of them lacked the lactone ring but maintained their cytotoxicity at, or under, the microM level.

  已经制备了几种与HT-29结肠癌的选择性抗肿瘤药9-脱氧-9-氧代-α-阿朴二十碳五烯酸甲酯有关的醛，并评估了它们对四种肿瘤细胞系的细胞毒活性（P-388，A- 549，HT-29和MEL-28）。他们所有人都没有内酯环，但将细胞毒性维持在microM水平或以下。
• First Total Synthesis of (+)-Podophyllic Aldehydes
  作者：Junki Ito、Daichi Sakuma、Yoshinori Nishii

  DOI：10.1246/cl.141061

  日期：2015.3.5

  The first total synthesis of three (+)-podophyllic aldehydes was achieved in a highly enantiocontrolled manner. Key steps include the organocatalyzed highly enantioselective cyclopropanation and Lewis acid-mediated chiral transfer ring expansion with excellent level of stereoinduction. This method can alternatively provide (+)- and (−)-podophyllic aldehydes by switching the organocatalyst in the asymmetric cyclopropanation.

  首次实现了三种(+)-鬼臼毒素醛的完全合成，采用了高度对映控制的方式。关键步骤包括通过有机催化的高度对映选择性环丙烷化和路易斯酸介导的手性传递环扩张，具有出色的立体诱导水平。通过在不对称环丙烷化步骤中切换有机催化剂，此方法可以交替提供(+)-和(−)-鬼臼毒素醛。
• Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring
  作者：Marina Gordaliza、MaAngeles Castro、JoséMa Miguel del Corral、MaLuisa López-Vázquez、Pablo A. García、Arturo San Feliciano、MaDolores García-Grávalos、Howard Broughton

  DOI：10.1016/s0040-4020(97)10042-4

  日期：1997.11

  Several cyclolignans lacking of the lactone moiety can easily be prepared from naturally occurring lignans such as podophyllotoxin and deoxypodophyllotoxin by simple chemical transformations. Their cytotoxicity has been studied in four tumoral cell lines. Most of the compounds show similar effects in all the neoplastic systems tested, except the aldehyde 9 (methyl 9-deoxy-9-oxo-alpha-apopicropodophyllate) and the hydrazones 16 and 17 which show a highly selective cytotoxicity towards HT-29 human colon carcinoma. Additionally, several molecular modeling studies have been done with aldehyde 9 and the corresponding saturated aldehyde 13 in comparison with podophyllotoxin. (C) 1997 Elsevier Science Ltd.
• Synthesis and cytotoxic evaluation of C-9 oxidized podophyllotoxin derivatives
  作者：M Angeles Castro、José M. Miguel del Corral、Marina Gordaliza、Pablo A. García、M Antonia Gómez-Zurita、Arturo San Feliciano

  DOI：10.1016/j.bmc.2006.12.008

  日期：2007.2

  A series of podophyllotoxin and podophyllic aldehyde derivatives, lacking the lactone ring and oxidized at C-9 position, has been prepared. The functionalities considered at C-9 were carboxylic acids and several derivatives such as esters, amides, nitriles or anhydrides. The synthesized compounds were cytotoxic at the micromolar level, though less potent and selective than the parent compounds, revealing

  已经制备了一系列缺乏内酯环并且在C-9位被氧化的鬼臼毒素和鬼臼醛衍生物。C-9处考虑的官能团是羧酸和几种衍生物，例如酯，酰胺，腈或酸酐。合成的化合物在微摩尔水平上具有细胞毒性，尽管其效力和选择性均低于母体化合物，从而揭示了C-9亲电特性对这些环木脂素的效力和选择性的影响。