3-(4-hydroxyphenyl)-N-methoxy-N-methylpropanamide | 827331-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(4-hydroxyphenyl)-N-methoxy-N-methylpropanamide
• CAS: 827331-49-7
• 化学式: C₁₁H₁₅NO₃
• mdl: MFCD24391298
• 分子量: 209.245
• InChiKey: ILKGJCGKLZSOEF-UHFFFAOYSA-N

物化性质

• 沸点：
  335.2±44.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenyl)-N-methoxy-N-methylpropanamide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以77%的产率得到3-(4-羟基-苯基)-丙醛
  参考文献：
  名称：

  Bioactive Pseudopeptidic Analogues and Cyclostereoisomers of Osteogenic Growth Peptide C-Terminal Pentapeptide, OGP(10−14)

  摘要：

  The osteogenic growth peptide (OGP) is a key factor in the mechanism of the systemic osteogenic response to local bone marrow injury. When administered an vivo, OGP stimulates osteogenesis and hematopoiesis. The C-terminal pentapeptide OGP(10-14) is the minimal amino acid sequence that retains the full OGP-like activity. Apparently, it is also the physiologic active form of OGP. Residues Tyr(10), Phe(12), Gly(13), and Gly(14) of OGP are essential for the OGP(10-14) activity. The present study explored the functional role of the peptide bonds, carboxyl and amino terminal groups, and conformational freedom in OGP(10-14). Transformations replacing the peptide bonds with surrogates such as Psi(CH2Me), Psi(CONMe), and Psi(CH2CH2) demonstrated that amide bonds do not contribute significantly to OGP(10-14) bioactivity. End-to-end cyclization yielded the fully bioactive cyclic pentapeptide c(Tyr-Gly-Phe-Gly-Gly). The retroinverso analogue c(Gly-Gly phe-Gly-tyr), a cyclostereoisomer of c(Tyr-Gly-Phe-Gly-Gly), is at least as potent as the parent cyclic pentapeptide. The unique structure-activity relations revealed in this study suggest that the spatial presentation of the Tyr and Phe side chains has a major role in the productive interaction of OGP(10-14) and its truncated and conformationally constrained analogues with their cognate cellular target.

  DOI：

  10.1021/jm010479l
• 作为产物：
  描述：

  对羟基苯丙酸 、 二甲羟胺盐酸盐 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 以99%的产率得到3-(4-hydroxyphenyl)-N-methoxy-N-methylpropanamide
  参考文献：
  名称：

  通过 Au(I) 催化的 Meyer-Schuster 重排高效全合成三种阿尔卑斯类化合物

  摘要：

  报道了三种结构相关的天然产物：脱氧alpinoid B、脱氧alpinoid A和alpinoid F的全合成，并且每种都以Au(I)催化的Meyer-Schuster重排为关键步骤。 Alpinoid F的合成为首次报道。这些天然产物的合成均表现出有效的抗癌活性，并且易于制备结构类似物。

  DOI：

  10.1016/j.tetlet.2022.154015

文献信息

• One-Pot, Enantioselective Synthesis of 2,3-Dihydroazulen-6(1<i>H</i>)-one: A Concise Access to the Core Structure of<i>Cephalotaxus</i>Norditerpenes
  作者：Yongsheng Zheng、Ebrahim H. Ghazvini Zadeh、Yu Yuan

  DOI：10.1002/ejoc.201600321

  日期：2016.4

  A one-pot enantioselective synthesis of cis-substituted 2,3-dihydroazulen-6(1H)-one is described. In this cascade reaction, an organocatalyzed asymmetric Michael reaction furnishes a highly optically pure nitrobutylphenol intermediate, which is converted into an annulated tropone species by sequential oxidative dearomatization, conjugate addition, electrocyclic ring opening and nitrous acid elimination

  描述了顺式取代的 2,3-dihydroazulen-6(1H)-one 的一锅对映选择性合成。在该级联反应中，有机催化的不对称迈克尔反应提供了高度光学纯的硝基丁基苯酚中间体，通过在同一反应容器中依次进行氧化脱芳构化、共轭加成、电环开环和亚硝酸消除，将其转化为环化的托酮类物质。脂肪族和芳香族硝基烯烃都是一锅反应的良好底物，该协议似乎也适用于各种苯丙醛。在不对称取代的苯丙醛的情况下，区域选择性可能由取代基的空间和电子特性决定。
• Enantioselective Synthesis of Cyclohexadienone Containing Spiroketals via DyKat Ketalization/oxa-Michael Addition Cascade
  作者：Reddy Rajasekhar Reddy、Shibaram Panda、Prasanta Ghorai

  DOI：10.1021/acs.joc.9b00371

  日期：2019.5.3

  An oxidative dearomatization of phenol followed by a dynamic kinetic (DyKat) ketalization/oxa-Michael addition cascade using cinchona alkaloid-based chiral bifunctional amino-squaramide catalysts is reported. A broad array of sterically hindered [5,5]-spiroketals attached to a cyclohexadienone moiety in spiro-fashion is synthesized in an enantiopure form. Further, the methodology was optimized and

  报道了使用金鸡纳生物碱基手性双官能氨基-方酸酰胺催化剂对苯酚进行氧化脱芳香化反应，然后进行动态动力学（DyKat）缩酮化/ oxa-Michael加成级联反应。以对映体纯净的形式合成了各种以螺旋形式连接到环己二烯酮部分的位阻[5,5]螺酮。此外，该方法进行了优化，并扩展到螺旋时尚中连接到环己二烯酮部分的相应苯并[5,5]-螺酮。通常，获得了良好的收率和优异的非对映选择性和对映选择性（高达20：1 dr和高达99％ee）。
• Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones
  作者：Aimee K. Clarke、William P. Unsworth、Richard J.K. Taylor

  DOI：10.1016/j.tet.2018.02.003

  日期：2018.9

  The first study of the divergent reactivity of phenol/anisole-tethered donor-acceptor α-diazoketones is described. Four distinct product classes were shown to be accessible from closely related α-diazoketone precursors, with the reaction outcome dependent on the nature of the oxygen substituent on the phenol/anisole ring and the catalyst used to decompose the diazo group. Anisole and TBS-protected

  描述了对苯酚/茴香醚系的供体-受体α-二氮杂酮的发散反应性的第一项研究。已显示可从密切相关的α-重氮酮前体中获得四种不同的产物类别，其反应结果取决于苯酚/茴香醚环上的氧取代基的性质以及用于分解重氮基团的催化剂。苯甲醚和TBS保护的衍生物选择性地产生三种产物类型（环丙烷，四氢萘酮和1,2-二羰基），而酚则选择性地产生螺环二烯酮。
• An Oxidative Prins-Pinacol Tandem Process and its Application to the synthesis of (−)-Platensimycin
  作者：Marc-André Beaulieu、Cyrille Sabot、Nabil Achache、Kimiaka C. Guérard、Sylvain Canesi

  DOI：10.1002/chem.201001813

  日期：——

  Center stage: An oxidative Prins–pinacol tandem process mediated by a hypervalent iodine reagent has been accomplished. The strategy allows rapid access to highly functionalized spirocyclic cores (see scheme) present in many natural products. A first application to the formal synthesis of (−)‐platensimycin has been achieved.

  中心阶段：已经完成了由高价碘试剂介导的氧化Prins-频哪醇串联过程。该策略允许快速访问许多天然产品中存在的高度官能化的螺环核（请参阅方案）。（-）-平台霉素的形式合成已获得了首次应用。